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Walk the Line
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For the song, see I Walk the Line. For other uses, see Walk the Line (disambiguation).
Walk the Line
Theatrical release poster
Directed by
James Mangold
Produced by
James Keach
Cathy Konrad
Screenplay by
Gill Dennis
James Mangold
Based on
Man in Black: His Own Story in His Own Words and Cash: The Autobiography
by Johnny Cash
Starring
Joaquin Phoenix
Reese Witherspoon
Ginnifer Goodwin
Robert Patrick
Dallas Roberts
Music by
T Bone Burnett
Cinematography
Phedon Papamichael
Edited by
Michael McCusker
Production
company
Fox 2000 Pictures
Distributed by
20th Century Fox
Release date
September 4, 2005 (2005-09-04) (Telluride Film Festival)
November 18, 2005 (2005-11-18) (United States)
Running time
136 minutes
(theatrical cut)
153 minutes
(extended cut)
Country
United States
Language
English
Budget
$28 million[1]
Box office
$186.4 million
Walk the Line is a 2005 American biographical drama film directed by James Mangold. The screenplay, written by Mangold and Gill Dennis, is based on two autobiographies authored by singer-songwriter Johnny Cash—Man in Black: His Own Story in His Own Words and Cash: The Autobiography. The film follows Cash's early life, his romance with June Carter, and his ascent to the country music scene. It stars Joaquin Phoenix as Cash, Reese Witherspoon as Carter, Ginnifer Goodwin as Vivian Liberto, and Robert Patrick as Cash's father.
Walk the Line previewed at the Telluride Film Festival on September 4, 2005, and went into wide release on November 18. The film was nominated for five Oscars at the 78th Academy Awards, including Best Actor (Phoenix), Best Actress (Witherspoon, which she won), and Best Costume Design (Arianne Phillips). The film grossed more than $186 million worldwide.
Contents
[hide]
1 Plot
2 Cast
3 Development and pre-production
4 Release
4.1 Box office
4.2 Reception
4.3 Accolades
5 Home media
6 Soundtrack
7 References
8 External links
Plot[edit]
In 1968, as an audience of inmates at Folsom State Prison cheer for Johnny Cash's band, he waits backstage near a table saw, reminding him of his early life.
In 1944, Johnny, then known as J.R., is raised on a cotton farm in Dyess, Arkansas with his brother Jack, father Ray, and mother Carrie. J.R. is known for his singing of hymns, while his brother Jack trains himself to become a pastor. While Jack is sawing wood for a neighbor with a table saw, J.R. goes fishing until he is spotted and reprimanded by his father for wandering off. Both J.R. and Ray return home to see Jack dying after being severely injured by the saw in an accident. In 1950, J.R. enlists in the Air Force as Johnny Cash, and is stationed in West Germany. He purchases a guitar, and in 1952, finds solace in writing songs, one of which he develops as "Folsom Prison Blues".
After his discharge, Cash returns to the United States and marries his girlfriend, Vivian Liberto. The couple moves to Memphis, Tennessee, where Cash works as a door-to-door salesman to support his growing family. He walks past a recording studio, which inspires him to organize a band to play gospel music. Cash's band auditions for Sam Phillips, the owner of Sun Records. After they play "Folsom Prison Blues", the band receives a contract, and launch to stardom at the beginning of the rock and roll era.
The band begins touring as Johnny Cash and the Tennessee Two. On tour, Johnny meets June Carter, with whom he falls in love. Cash begins spending more time with June, who divorces her first husband, Carl Smith. After his attempt to woo June fails, Cash starts abusing drugs and alcohol. After his behavior reaches a bottom during a performance with June, they separate.
Later, over Vivian's objections, Johnny persuades June to come out of semi-retirement, and tour with him. The tour is a success, but backstage, Vivian becomes critical of June's influence. After one performance in Las Vegas, Johnny and June sleep together. The next morning, she notices Johnny taking pills, and doubts her choices. At that evening's concert, Johnny, upset by June's apparent rejection, behaves erratically, and eventually passes out on stage. June disposes of Johnny's drugs, and begins to write "Ring of Fire", describing her feelings for him and her pain at watching him descend into addiction.
Returning to California, Cash travels to Mexico to purchase more drugs, and is arrested. Cash's marriage to Vivian implodes; the pair divorce and Cash moves to Nashville in 1966. Trying to reconcile with June, Johnny purchases a large house near a lake in Hendersonville. His parents and the extended Carter family arrive for Thanksgiving, at which time Ray dismisses his son's achievements and behavior. After the meal, June's mother encourages her daughter to help Cash. He goes into detox and wakes with June; she says they have been given a second chance. Though not married, the two begin spending most of their time with each other.
Cash discovers that most of his fan mail is from prisoners, who are impressed with his outlaw image. He proposes to Columbia Records that he will record an album live inside Folsom Prison. Despite Columbia's doubts, Cash says that he will perform, and his label can use the tapes if they wish. At the Folsom Prison concert, Cash says that he has been sympathetic to prisoners, explaining that his arrest for drug possession helped him to relate to them. With this success, Cash embarks on a tour with June and his band. On the bus, he stops to talk with June and proposes to her, but she turns him down. At the next concert, June says she will only speak with him on stage. Cash later performs "Ring of Fire" on stage. After the song, Cash invites June to a duet and stops in the middle, saying he cannot sing "Jackson" any more unless June agrees to marry him. June accepts and they share a passionate embrace on stage.
Cast[edit]
Joaquin Phoenix as Johnny Cash
Reese Witherspoon as June Carter
Ginnifer Goodwin as Vivian Liberto, Johnny's first wife
Robert Patrick as Ray Cash, Johnny's father
Hailey Anne Nelson as Rosanne Cash, Johnny's oldest daughter
Dallas Roberts as Sam Phillips, the founder, owner, and producer of Sun Records
Dan John Miller as Luther Perkins, Johnny's first guitarist
Johnny Holiday as Carl Perkins
Larry Bagby as Marshall Grant, Johnny's bassist
Shelby Lynne as Carrie Cash, Johnny's mother
Sandra Ellis Lafferty as Maybelle Addington Carter, June's mother
Tyler Hilton as Elvis Presley
Waylon Payne as Jerry Lee Lewis
Shooter Jennings as Waylon Jennings, Johnny's future bandmate
Clay Steakley as Fluke Holland, Johnny's drummer
Johnathan Rice as Roy Orbison
Lucas Till as Jack Cash, Johnny's brother
Ridge Canipe as young Johnny Cash
James Keach as Folsom Prison Warden
Development and pre-production[edit]
The film has its origins in a 1993 episode of Dr. Quinn, Medicine Woman.,[2] That year, Cash was a guest star on the show, where he and June Carter became friends with Jane Seymour, the star of the show, and Seymour's husband James Keach who was directing the episode. By the mid-1990s, Cash had asked Keach to make a film of his life; he and Seymour began the process with a series of interviews.[2] In 1997, the interviews had been the basis of a screenplay written by Gill Dennis, with input from Keach; two years later, still lacking any studio interest, Keach contacted James Mangold, who had been "angling to become involved in the project for two years."[2] Mangold and his wife, producer Cathy Konrad, developed the script for Sony, and by 2001, they had a script they thought they could pitch to a studio. Sony and others turned it down, but Fox 2000 agreed to make the film.[2]
The film was in part based on two autobiographies, both of which were optioned: Man in Black (1975) and Cash: The Autobiography (1997), though the film "burrows deep into painful territory that Mr. Cash barely explored."[2]
Phoenix met Cash months before hearing about the film. When Phoenix read the script, he felt there were at least ten other actors who would be better in the role.[3] To prepare for her role as June Carter, Witherspoon watched several videos of the singer; she also listened to her singing and telling stories to get her voice right.[4]
Release[edit]
Box office[edit]
Walk the Line was released on November 18, 2005, in 2,961 theaters, grossing $22.3 million on its opening weekend. It went on to earn $119.5 million in North America and $66.9 million in the rest of the world for a total of $186.4 million, well above its $28 million budget, making it a box office success.[5] It was the all-time highest grossing music biopic until Straight Outta Compton surpassed it in 2015.
Reception[edit]
Critics generally responded with positive reviews, garnering an 82% on Rotten Tomatoes. The two lead performances received rave reviews, particularly Witherspoon's, whose performance is described by critics as her best work to date. Roger Ebert praised Witherspoon for her "boundless energy" and predicted her to win the Academy Award for Best Actress.[6][7] In her review for the Los Angeles Times, Carina Chocano wrote, "Joaquin Phoenix and Reese Witherspoon do first-rate work — they sing, they twang, they play new-to-them instruments, they crackle with wit and charisma, and they give off so much sexual heat it's a wonder they don't burst into flames".[8]
A. O. Scott, in his review for The New York Times, had problems with Phoenix's performance: "Even though his singing voice doesn't match the original - how could it? - he is most convincing in concert, when his shoulders tighten and he cocks his head to one side. Otherwise, he seems stuck in the kind of off-the-rack psychological straitjacket in which Hollywood likes to confine troubled geniuses".[9] In his review for Time, Richard Corliss wrote, "A lot of credit for Phoenix's performance has to go to Mangold, who has always been good at finding the bleak melodrama in taciturn souls ... If Mangold's new movie has a problem, it's that he and co-screenwriter Gill Dennis sometimes walk the lines of the inspirational biography too rigorously".[10]
Andrew Sarris, in his review for The New York Observer praised Witherspoon for her "spine-tingling feistiness", and wrote, "This feat has belatedly placed it (in my mind, at least) among a mere handful of more-than-Oscar-worthy performances this year".[11] Entertainment Weekly gave the film a "B+" rating and Owen Gleiberman wrote, "while Witherspoon, a fine singer herself, makes Carter immensely likable, a fountain of warmth and cheer, given how sweetly she meshes with Phoenix her romantic reticence isn't really filled in".[12] Baltimore Sun reviewer Michael Sragow wrote, "What Phoenix and Witherspoon accomplish in this movie is transcendent. They act with every bone and inch of flesh and facial plane, and each tone and waver of their voice. They do their own singing with a startling mastery of country music's narrative musicianship".[13] In his review for Sight and Sound, Mark Kermode wrote, "Standing ovations, too, for Witherspoon, who has perhaps the tougher task of lending depth and darkness to the role of June, whose frighteningly chipper stage act - a musical-comedy hybrid - constantly courts (but never marries) mockery".[14]
Some critics found the film too constrained by Hollywood plot formulas of love and loss, ignoring the last twenty years of Cash's life and other more socio-politically controversial reasons he was considered "the man in black".[15]
Rosanne Cash was critical of the film. She was upset "because it had the three most damaging events of [her] childhood: [her] parent's divorce, [her] father's drug addiction, and something else bad that [she] can't remember now". Furthermore, she said, "The movie was painful. The three of them [in the film] were not recognizable to me as my parents in any way. But the scenes were recognizable, and the storyline, so the whole thing was fraught with sadness because they all had just died, and I had this resistance to seeing the screen version of my childhood".[16]
Accolades[edit]
Main article: List of accolades received by Walk the Line
Academy Awards
1. Best Actress in a Leading Role (Reese Witherspoon)
Golden Globe Awards
1. Best Motion Picture – Musical or Comedy
2. Best Actor in a Leading Role – Musical or Comedy (Joaquin Phoenix)
3. Best Actress in a Leading Role – Musical or Comedy (Reese Witherspoon)
BAFTA Awards
1. Best Actress (Reese Witherspoon)
2. Best Sound
Witherspoon's performance was repeatedly recognized, including an Academy Award for Best Actress[17] and other awards such as:
BAFTA Award as Best Actress
Broadcast Film Critic Award as Best Actress
Golden Globe Award as Best Actress – Musical or Comedy
National Society of Film Critics Award as Best Actress
Online Film Critics Society award as Best Actress
Satellite Award as Best Actress – Musical or Comedy
Screen Actors Guild Award as Best Actress
Film critic Andrew Sarris ranked Walk the Line number seven in top films of 2005 and cited Reese Witherspoon as the best female performance of the year.[18] Witherspoon was also voted Favorite Leading Lady at the 2006 People's Choice Awards.[19] David Ansen of Newsweek ranked Witherspoon as one of the five best actresses of 2005.[20]
Home media[edit]
On February 28, 2006, a single-disc DVD and a two-disc collector edition DVD were released; these editions sold three million copies on their first day of release.[21] On March 25, 2008, a two-disc 'extended cut' DVD was released for region one. The feature on disc one is 17 minutes longer than the theatrical release, and disc two features eight extended musical sequences with introductions and documentaries about the making of the film. The film has been released on Blu-ray Disc in France, Sweden and the UK in the form of its extended cut. The American Blu-ray features the shorter theatrical cut.
Soundtrack[edit]
Main article: Walk the Line (soundtrack)
Wind-up Records released the soundtrack in November 2005. It featured nine songs performed by Joaquin Phoenix, four songs by Reese Witherspoon, two songs by Tyler Hilton, and one song each by Waylon Payne, Johnathan Rice, and Shooter Jennings. The album received a Grammy at the 49th Annual Grammy Awards for Best Compilation Soundtrack Album for Motion Pictures, Television or Other Visual Media.
References[edit]
Jump up ^ "Walk the Line (2005)". Boxofficemojo.com. Retrieved 2012-04-14.
^ Jump up to: a b c d e Waxman, Sharon (October 16, 2005). "The Secrets That Lie Beyond the Ring of Fire". The New York Times. Retrieved 2015-02-10.
Jump up ^ "Joaquin Phoenix Talks About 'Walk the Line'". Retrieved November 17, 2011.
Jump up ^ "Reese Witherspoon Talks About 'Walk the Line'". Retrieved November 17, 2011.
Jump up ^ "Walk the Line". Box Office Mojo. Retrieved 2009-01-27.
Jump up ^ Ebert, Roger (November 18, 2005). "Walk the Line". Chicago Sun-Times. Retrieved 2009-01-27.
Jump up ^ Ebert, Roger (February 18, 2006). "Ebert's Oscar Predictions (2006)". Chicago Sun-Times. Retrieved 2017-04-22.
Jump up ^ Chocano, Carina (November 18, 2005). "Walk the Line". Los Angeles Times. Archived from the original on 2008-06-16. Retrieved 2009-01-27.
Jump up ^ Scott, A. O. (November 18, 2005). "The Man in Black, on Stage and Off". The New York Times. Retrieved 2009-01-27.
Jump up ^ Corliss, Richard (November 18, 2005). "A Phoenix in the Ring of Fire". Time. Retrieved 2009-01-27.
Jump up ^ Sarris, Andrew (January 8, 2006). "Funny, Fiftysomething Pierce Returns as The Matador". The New York Observer. Retrieved 2009-01-27.
Jump up ^ Gleiberman, Owen (November 16, 2005). "Walk the Line". Entertainment Weekly. Retrieved 2009-01-27.
Jump up ^ Sragow, Michael (November 18, 2005). "A Walk to see and remember". Baltimore Sun.
Jump up ^ Kermode, Mark (February 2006). "Walk the Line". Sight and Sound. Retrieved 2009-01-27.
Jump up ^ Harsin, Jayson. "Walking the Fine Line". Bright Lights Film Journal. Retrieved 2012-04-14.
Jump up ^ Garfield, Simon (February 5, 2006). "Family ties". The Guardian. Retrieved March 7, 2018.
Jump up ^ "The 78th Academy Awards (2006) Nominees and Winners". oscars.org. Retrieved 2011-11-20.
Jump up ^ Sarris, Andrew (January 5, 2006). "Who and What I Liked in 2005: Viggo, Violence, Reese, 2046". The New York Observer. Retrieved 2009-01-27.
Jump up ^ "People's Choice Awards". Movie City News. Archived from the original on 2007-08-14. Retrieved 2009-01-27.
Jump up ^ Ansen, David (December 19, 2005). "The Five Best Actresses". Newsweek. Retrieved 2009-01-27.
Jump up ^ "Walk the Line (2005)". MovieWeb. Retrieved 2015-04-09.
External links[edit]
Wikiquote has quotations related to: Walk the Line
Official website
Walk the Line on IMDb
Walk the Line at AllMovie
Walk the Line at Box Office Mojo
Walk the Line at Rotten Tomatoes
Walk the Line at Metacritic
[show]
v
t
e
Johnny Cash
Studio albums
With His Hot and Blue Guitar
Sings the Songs That Made Him Famous
The Fabulous Johnny Cash
Greatest!
Songs of Our Soil
Sings Hank Williams
Now, There Was a Song!
Now Here's Johnny Cash
The Sound of Johnny Cash
All Aboard the Blue Train
Ring of Fire: The Best of Johnny Cash
The Original Sun Sound of Johnny Cash
I Walk the Line
Orange Blossom Special
Everybody Loves a Nut
Happiness Is You
Old Golden Throat
More of Old Golden Throat
Hello, I'm Johnny Cash
The World of Johnny Cash
Man in Black
A Thing Called Love
Any Old Wind That Blows
Ragged Old Flag
The Junkie and the Juicehead Minus Me
John R. Cash
Look at Them Beans
One Piece at a Time
The Last Gunfighter Ballad
I Would Like to See You Again
Gone Girl
Silver
Rockabilly Blues
The Baron
The Adventures of Johnny Cash
Johnny 99
Rainbow
Johnny Cash Is Coming to Town
Classic Cash: Hall of Fame Series
Water from the Wells of Home
Boom Chicka Boom
The Mystery of Life
American Recordings
Unchained
American III: Solitary Man
American IV: The Man Comes Around
Personal File
American V: A Hundred Highways
American VI: Ain't No Grave
Out Among the Stars
Concept albums
Ride This Train
Blood, Sweat and Tears
Bitter Tears: Ballads of the American Indian
Sings the Ballads of the True West
From Sea to Shining Sea
America: A 200-Year Salute in Story and Song
The Johnny Cash Children's Album
The Rambler
Gospel albums
Hymns by Johnny Cash
Hymns from the Heart
The Holy Land
The Gospel Road
Sings Precious Memories
A Believer Sings the Truth
Believe in Him
Return to the Promised Land
My Mother's Hymn Book
Christmas albums
The Christmas Spirit
The Johnny Cash Family Christmas
Classic Christmas
Johnny Cash Country Christmas
Collaborations
The Lure of the Grand Canyon
Carryin' On with Johnny Cash and June Carter
Johnny Cash and His Woman
The Legend of Jesse James
Million Dollar Quartet
The Survivors Live
Highwayman
Class of '55
Heroes
Highwayman 2
The Road Goes on Forever
VH1 Storytellers
Live albums
At Folsom Prison
At San Quentin
The Johnny Cash Show
På Österåker
Strawberry Cake
Koncert v Praze (In Prague–Live)
At Madison Square Garden
A Concert Behind Prison Walls
Non-gospel soundtracks
I Walk the Line
Little Fauss and Big Halsy
Compilations
Greatest Hits, Vol. 1
Heart of Cash
Greatest Hits, Vol. 2
Sunday Morning Coming Down
International Superstar
Five Feet High and Rising
Destination Victoria Station
Greatest Hits, Vol. 3
The Unissued Johnny Cash
Johnny & June
Tall Man
Encore
Biggest Hits
The Man in Black 1954–1958
The Man in Black 1959–1962
Come Along and Ride This Train
The Essential Johnny Cash (1992)
Wanted Man
The Man in Black 1963–1969
The Man in Black – His Greatest Hits
16 Biggest Hits
Love, God, Murder
The Essential Johnny Cash (2002)
Unearthed
The Legend
The Legend of Johnny Cash
Johnny Cash: Patriot
16 Biggest Hits: Johnny Cash & June Carter Cash
The Legend of Johnny Cash Vol. II
The Complete Columbia Album Collection
Songs
"25 Minutes to Go"
"Seasons of My Heart"
"Any Old Wind That Blows"
"A Wonderful Time Up There"
"The Ballad of Boot Hill"
"The Ballad of Ira Hayes"
"Ballad of a Teenage Queen"
"Big River"
"Blistered"
"A Boy Named Sue"
"Busted"
"Cat's in the Cradle"
"Cocaine Blues"
"Cry! Cry! Cry!"
"Daddy Sang Bass"
"Dark as a Dungeon"
"Don't Take Your Guns to Town"
"Engine 143"
"Flesh and Blood"
"The Folk Singer"
"Folsom Prison Blues"
"Forty Shades of Green"
"Get Rhythm"
"Give My Love to Rose"
"Goodnight, Irene"
"Green, Green Grass of Home"
"Greystone Chapel"
"Guess Things Happen That Way"
"Hey, Porter"
"Home of the Blues"
"Hurt"
"I Couldn't Keep from Crying"
"I Love You Because"
"I Still Miss Someone"
"I Walk the Line"
"If I Had a Hammer"
"If I Were a Carpenter"
"In My Life"
"In the Jailhouse Now"
"It Ain't Me Babe"
"Jackson"
"Kate"
"The Man Comes Around"
"Man in Black"
"The Matador"
"Oh Lonesome Me"
"One Piece at a Time"
"Oney"
"Orange Blossom Special"
"The One on the Right Is on the Left"
"Remember the Alamo"
"(Ghost) Riders in the Sky"
"Ring of Fire"
"Rock Island Line"
"So Doggone Lonesome"
"Sunday Mornin' Comin' Down"
"Tennessee Flat Top Box"
"There Ain't No Good Chain Gang"
"A Thing Called Love"
"Understand Your Man"
"What Is Truth"
"What'd I Say"
Television
The Johnny Cash Show
Family
June Carter Cash
John Carter Cash
Rosanne Cash
Carlene Carter
Tommy Cash
Carter Family
Related
Albums discography
Singles discography
Sun Records discography
The Highwaymen
Carter Family Fold
Man in Black: His Own Story in His Own Words
Cash: The Autobiography
Johnny Cash! The Man, His World, His Music
Walk the Line
We Walk the Line: A Celebration of the Music of Johnny Cash
Ring of Fire (2013 film)
Ring of Fire (musical)
My Father and the Man in Black
Forever Words
Dyess, Arkansas
The Tennessee Three
Book
[show]
v
t
e
Films directed by James Mangold
Heavy (1995)
Cop Land (1997)
Girl, Interrupted (1999)
Kate & Leopold (2001)
Identity (2003)
Walk the Line (2005)
3:10 to Yuma (2007)
Knight and Day (2010)
The Wolverine (2013)
Logan (2017)
[show]
Awards for Walk the Line
[show]
v
t
e
Golden Globe Award for Best Motion Picture – Musical or Comedy
An American in Paris (1951)
With a Song in My Heart (1952)
Carmen Jones (1954)
Guys and Dolls (1955)
The King and I (1956)
Les Girls (1957)
Gigi / Auntie Mame (1958)
Porgy and Bess / Some Like It Hot (1959)
Song Without End / The Apartment (1960)
West Side Story / A Majority of One (1961)
The Music Man / That Touch of Mink (1962)
Tom Jones (1963)
My Fair Lady (1964)
The Sound of Music (1965)
The Russians Are Coming, the Russians Are Coming (1966)
The Graduate (1967)
Oliver! (1968)
The Secret of Santa Vittoria (1969)
MASH (1970)
Fiddler on the Roof (1971)
Cabaret (1972)
American Graffiti (1973)
The Longest Yard (1974)
The Sunshine Boys (1975)
A Star Is Born (1976)
The Goodbye Girl (1977)
Heaven Can Wait (1978)
Breaking Away (1979)
Coal Miner's Daughter (1980)
Arthur (1981)
Tootsie (1982)
Yentl (1983)
Romancing the Stone (1984)
Prizzi's Honor (1985)
Hannah and Her Sisters (1986)
Hope and Glory (1987)
Working Girl (1988)
Driving Miss Daisy (1989)
Green Card (1990)
Beauty and the Beast (1991)
The Player (1992)
Mrs. Doubtfire (1993)
The Lion King (1994)
Babe (1995)
Evita (1996)
As Good as It Gets (1997)
Shakespeare in Love (1998)
Toy Story 2 (1999)
Almost Famous (2000)
Moulin Rouge! (2001)
Chicago (2002)
Lost in Translation (2003)
Sideways (2004)
Walk the Line (2005)
Dreamgirls (2006)
Sweeney Todd: The Demon Barber of Fleet Street (2007)
Vicky Cristina Barcelona (2008)
The Hangover (2009)
The Kids Are All Right (2010)
The Artist (2011)
Les Misérables (2012)
American Hustle (2013)
The Grand Budapest Hotel (2014)
The Martian (2015)
La La Land (2016)
Lady Bird (2017)
[show]
v
t
e
Satellite Award for Best Film
Musical or Comedy
(1996–2009, retired)
Evita (1996)
As Good as It Gets (1997)
Shakespeare in Love (1998)
Being John Malkovich (1999)
Nurse Betty (2000)
Moulin Rouge! (2001)
My Big Fat Greek Wedding (2002)
Lost in Translation (2003)
Sideways (2004)
Walk the Line (2005)
Dreamgirls (2006)
Juno (2007)
Happy-Go-Lucky (2008)
Nine (2009)
Motion Picture Drama
(1996–2009, retired)
Fargo (1996)
Titanic (1997)
The Thin Red Line (1998)
The Insider (1999)
Traffic (2000)
In the Bedroom (2001)
Far from Heaven (2002)
In America (2003)
Hotel Rwanda (2004)
Brokeback Mountain (2005)
The Departed (2006)
No Country for Old Men (2007)
Slumdog Millionaire (2008)
The Hurt Locker (2009)
Motion Picture
(2010–present)
The Social Network (2010)
The Descendants (2011)
Silver Linings Playbook (2012)
12 Years a Slave (2013)
Birdman or (The Unexpected Virtue of Ignorance) (2014)
Spotlight (2015)
La La Land / Manchester by the Sea (2016)
God's Own Country / Three Billboards Outside Ebbing, Missouri (2017)
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text:
Oxalic acid
From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
simplest dicarboxylic acid
Oxalic acid
Names
Preferred IUPAC name
Oxalic acid[1]
Systematic IUPAC name
Ethanedioic acid[1]
Other names
Wood bleach
Identifiers
CAS Number
144-62-7 (anhydrous) Y
6153-56-6 (dihydrate) N
3D model (JSmol)
Interactive image
3DMet B00059
Beilstein Reference
385686
ChEBI
CHEBI:16995 Y
ChEMBL
ChEMBL146755 Y
ChemSpider
946 Y
DrugBank
DB03902 Y
ECHA InfoCard 100.005.123
EC Number 205-634-3
Gmelin Reference
2208
KEGG
C00209 N
MeSH Oxalic+acid
PubChem CID
971
RTECS number RO2450000
UNII
9E7R5L6H31 Y
UN number 3261
InChI[show]
InChI=1S/C2H2O4/c3-1(4)2(5)6/h(H,3,4)(H,5,6) Y
Key: MUBZPKHOEPUJKR-UHFFFAOYSA-N Y
SMILES[show]
C(=O)(C(=O)O)O
Properties
Chemical formula
C2H2O4
Molar mass 90.03 g·mol−1
(anhydrous)
126.065 g mol−1 (dihydrate)
Appearance White crystals
Odor odorless
Density 1.90 g cm−3 (anhydrous, at 17 °C)[2]
1.653 g cm−3 (dihydrate)
Melting point 189 to 191 °C (372 to 376 °F; 462 to 464 K)
101.5 °C (214.7 °F; 374.6 K) dihydrate
Solubility in water
90-100 g/L (20 °C)[2]
Solubility 237 g/L (15 °C) in ethanol
14 g/L (15 °C) in diethyl ether [3]
Vapor pressure <0.001 mmHg (20 °C)[4]
Acidity (pKa) 1.25, 4.14[5]
Magnetic susceptibility (χ)
-60.05·10−6 cm3/mol
Pharmacology
ATCvet code
QP53AG03 (WHO)
Hazards
Main hazards corrosive
Safety data sheet External MSDS
NFPA 704
1
3
0
ACID
Flash point 166 °C (331 °F; 439 K)
Lethal dose or concentration (LD, LC):
LDLo (lowest published)
1000 mg/kg (dog, oral)
1400 mg/kg (rat)
7500 mg/kg (rat, oral)[6]
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 1 mg/m3[4]
REL (Recommended)
TWA 1 mg/m3 ST 2 mg/m3[4]
IDLH (Immediate danger)
500 mg/m3[4]
Related compounds
Related compounds
oxalyl chloride
disodium oxalate
calcium oxalate
phenyl oxalate ester
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is Y N ?)
Infobox references
Oxalic acid is an organic compound with the formula C2H2O4. It is a colorless crystalline solid that forms a colorless solution in water. Its condensed formula is HOOCCOOH, reflecting its classification as the simplest dicarboxylic acid.
Its acid strength is much greater than that of acetic acid. Oxalic acid is a reducing agent[7] and its conjugate base, known as oxalate (C
2O2−
4), is a chelating agent for metal cations. Typically, oxalic acid occurs as the dihydrate with the formula C2H2O4·2H2O.
It occurs naturally in many foods, but excessive ingestion of oxalic acid or prolonged skin contact can be dangerous.
Its name comes from the fact that early investigators isolated oxalic acid from wood-sorrel (Oxalis) flowering plants.
Contents
1 History
2 Preparation
2.1 Laboratory methods
3 Structure
4 Reactions
5 Occurrence
5.1 Biosynthesis
5.2 Occurrence in foods and plants
5.3 Other
6 Biochemistry
7 Applications
7.1 Cleaning
7.2 Extractive metallurgy
7.3 Niche uses
8 Content in food items
9 Toxicity of concentrated oxalic acid
10 References
11 External links
History[edit]
The preparation of salts of oxalic acid from plants had been known, at the latest, since 1745, when the Dutch botanist and physician Herman Boerhaave isolated a salt from sorrel.[8] By 1773, François Pierre Savary of Fribourg, Switzerland had isolated oxalic acid from its salt in sorrel.[9]
In 1776, Swedish chemists Carl Wilhelm Scheele and Torbern Olof Bergman[10] produced oxalic acid by reacting sugar with concentrated nitric acid; Scheele called the acid that resulted socker-syra or såcker-syra (sugar acid). By 1784, Scheele had shown that "sugar acid" and oxalic acid from natural sources were identical.[11]
In 1824, the German chemist Friedrich Wöhler obtained oxalic acid by reacting cyanogen with ammonia in aqueous solution.[12] This experiment may represent the first synthesis of a natural product.[13]
Preparation[edit]
Oxalic acid is mainly manufactured by the oxidation of carbohydrates or glucose using nitric acid or air in the presence of vanadium pentoxide. A variety of precursors can be used including glycolic acid and ethylene glycol.[14] A newer method entails oxidative carbonylation of alcohols to give the diesters of oxalic acid:
4 ROH + 4 CO + O2 → 2 (CO2R)2 + 2 H2O
These diesters are subsequently hydrolyzed to oxalic acid. Approximately 120,000 tonnes are produced annually.[13]
Historically oxalic acid was obtained exclusively by using caustics, such as sodium or potassium hydroxide, on sawdust.[15]
Laboratory methods[edit]
Although it can be readily purchased, oxalic acid can be prepared in the laboratory by oxidizing sucrose using nitric acid in the presence of a small amount of vanadium pentoxide as a catalyst.[16]
The hydrated solid can be dehydrated with heat or by azeotropic distillation.[17]
Developed in the Netherlands, an electrocatalysis by a copper complex helps reduce carbon dioxide to oxalic acid;[18] this conversion uses carbon dioxide as a feedstock to generate oxalic acid.
Structure[edit]
Anhydrous oxalic acid exists as two polymorphs; in one the hydrogen-bonding results in a chain-like structure whereas the hydrogen bonding pattern in the other form defines a sheet-like structure.[19] Because the anhydrous material is both acidic and hydrophilic (water seeking), it is used in esterifications.
Reactions[edit]
Oxalic acid is a relatively strong acid, despite being a carboxylic acid:
C2O4H2 ⇌ C2O4H− + H+ pKa = 1.27
C2O4H− ⇌ C
2O2−
4 + H+ pKa = 4.27
Oxalic acid undergoes many of the reactions characteristic of other carboxylic acids. It forms esters such as dimethyl oxalate (m.p. 52.5 to 53.5 °C (126.5 to 128.3 °F)).[20] It forms an acid chloride called oxalyl chloride.
Oxalate, the conjugate base of oxalic acid, is an excellent ligand for metal ions, e.g. the drug oxaliplatin.
Oxalic acid and oxalates can be oxidized by permanganate in an autocatalytic reaction.[21]
Occurrence[edit]
Biosynthesis[edit]
At least two pathways exist for the enzyme-mediated formation of oxalate. In one pathway, oxaloacetate, a component of the Krebs citric acid cycle, is hydrolyzed to oxalate and acetic acid by the enzyme oxaloacetase:[22]
[O2CC(O)CH2CO2]2− + H2O → C
2O2−
4 + CH
3CO−
2 + H+
It also arises from the dehydrogenation of glycolic acid, which is produced by the metabolism of ethylene glycol.
Occurrence in foods and plants[edit]
Calcium oxalate is the most common component of kidney stones. Early investigators isolated oxalic acid from wood-sorrel (Oxalis). Members of the spinach family and the brassicas (cabbage, broccoli, brussels sprouts) are high in oxalates, as are sorrel and umbellifers like parsley.[23] Rhubarb leaves contain about 0.5% oxalic acid, and jack-in-the-pulpit (Arisaema triphyllum) contains calcium oxalate crystals. Similarly, the Virginia creeper, a common decorative vine, produces oxalic acid in its berries as well as oxalite crystals in the sap, in the form of raphides. Bacteria produce oxalates from oxidation of carbohydrates.[13]
Plants of the genus Fenestraria produce optical fibers made from crystalline oxalic acid to transmit light to subterranean photosynthetic sites.[24]
Carambola, also known as starfruit, also contains oxalic acid along with caramboxin.
The formation of naturally occurring calcium oxalate patinas on certain limestone and marble statues and monuments has been proposed to be caused by the chemical reaction of the carbonate stone with oxalic acid secreted by lichen or other microorganisms.[25][26]
Other[edit]
Oxidized bitumen or bitumen exposed to gamma rays also contains oxalic acid among its degradation products. Oxalic acid may increase the leaching of radionuclides conditioned in bitumen for radioactive waste disposal.[27]
Biochemistry[edit]
The conjugate base of oxalic acid is the hydrogenoxalate anion, and its conjugate base (oxalate) is a competitive inhibitor of the lactate dehydrogenase (LDH) enzyme.[28] LDH catalyses the conversion of pyruvate to lactic acid (end product of the fermentation (anaerobic) process) oxidising the coenzyme NADH to NAD+ and H+ concurrently. Restoring NAD+ levels is essential to the continuation of anaerobic energy metabolism through glycolysis. As cancer cells preferentially use anaerobic metabolism (see Warburg effect) inhibition of LDH has been shown to inhibit tumor formation and growth,[29] thus is an interesting potential course of cancer treatment.
Applications[edit]
About 25% of produced oxalic acid will be used as a mordant in dyeing processes. It is used in bleaches, especially for pulpwood. It is also used in baking powder[13] and as a third reagent in silica analysis instruments.
Cleaning[edit]
Oxalic acid's main applications include cleaning or bleaching, especially for the removal of rust (iron complexing agent). Bar Keepers Friend is an example of a household cleaner containing oxalic acid. Its utility in rust removal agents is due to its forming a stable, water-soluble salt with ferric iron, ferrioxalate ion.
Extractive metallurgy[edit]
Oxalic acid is an important reagent in lanthanide chemistry. Hydrated lanthanide oxalates form readily in very strongly acidic solutions in a densely crystalline, easily filtered form, largely free of contamination by nonlanthanide elements. Thermal decomposition of these oxalate gives the oxides, which is the most commonly marketed form of these elements.
Niche uses[edit]
Honeybee coated with oxalate crystals
Vaporized oxalic acid, or a 3.2% solution of oxalic acid in sugar syrup, is used by some beekeepers as a miticide against the parasitic varroa mite.[30]
Oxalic acid is rubbed onto completed marble sculptures to seal the surface and introduce a shine. Oxalic acid is also used to clean iron and manganese deposits from quartz crystals.[31][32]
Oxalic acid is used as a bleach for wood, removing black stains caused by dissolved iron that binds to the wood during water penetration.
Oxalic acid is sometimes used in the aluminum anodizing process, with or without sulfuric acid. Compared to sulfuric acid anodizing, the coatings obtained are thinner and exhibit lower surface roughness.
Content in food items[edit]
Vegetable
Oxalic acid
(g/100 g)[33][clarification needed]
Amaranth 1.09
Asparagus 0.13
Beans, snap 0.36
Beet leaves 0.61
Broccoli 0.19
Brussels sprouts 0.36
Cabbage 0.10
Carrot 0.50
Cassava 1.26
Cauliflower 0.15
Celery 0.19
Chicory 0.2
Chives 1.48
Collards 0.45
Coriander 0.01
Corn, sweet 0.01
Cucumber 0.02
Eggplant 0.19
Endive 0.11
Garlic 0.36
Kale 0.02
Lettuce 0.33
Okra 0.05
Onion 0.05
Parsley 1.70
Parsnip 0.04
Pea 0.05
Bell pepper 0.04
Potato 0.05
Purslane 1.31
Radish 0.48
Rhubarb leaves 0.52[34]
Rutabaga 0.03
Spinach 0.97 (ranges from .65 to 1.3 grams per 100 grams on fresh weight basis)[35]
Squash 0.02
Sweet potato 0.24
Tomato 0.05
Turnip 0.21
Turnip greens 0.05
Watercress 0.31
Toxicity of concentrated oxalic acid[edit]
Oxalic acid in concentrated form can have harmful effects through contact and if ingested; manufacturers provide details in Material Safety Data Sheets (MSDS). It is not identified as mutagenic or carcinogenic; there is a possible risk of congenital malformation in the fetus; may be harmful if inhaled, and is extremely destructive to tissue of mucous membranes and upper respiratory tract; harmful if swallowed; harmful to and destructive of tissue and causes burns if absorbed through the skin or is in contact with the eyes. Symptoms and effects include a burning sensation, cough, wheezing, laryngitis, shortness of breath, spasm, inflammation and edema of the larynx, inflammation and edema of the bronchi, pneumonitis, pulmonary edema.[36]
In humans, ingested oxalic acid has an oral LDLo (lowest published lethal dose) of 600 mg/kg.[37] It has been reported that the lethal oral dose is 15 to 30 grams.[38]
The toxicity of oxalic acid is due to kidney failure caused by precipitation of solid calcium oxalate,[39] the main component of calcium kidney stones. Oxalic acid can also cause joint pain due to the formation of similar precipitates in the joints. Ingestion of ethylene glycol results in oxalic acid as a metabolite which can also cause acute kidney failure.
References[edit]
^ Jump up to: a b "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. P001–P004. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
^ Jump up to: a b Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
Jump up ^ Radiant Agro Chem. "Oxalic Acid MSDS".
^ Jump up to: a b c d "NIOSH Pocket Guide to Chemical Hazards #0474". National Institute for Occupational Safety and Health (NIOSH).
Jump up ^ Bjerrum, J., et al. (1958) Stability Constants, Chemical Society, London.
Jump up ^ "Oxalic acid". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
Jump up ^ Ullmann's Encyclopedia of Industrial Chemistry. Wiley. 2005. pp. 17624/28029. doi:10.1002/14356007. ISBN 9783527306732.
Jump up ^ See:
Herman Boerhaave, Elementa Chemiae (Basil, Switzerland: Johann Rudolph Im-hoff, 1745), volume 2, pp. 35-38. (in Latin) From p. 35: "Processus VII. Sal nativum plantarum paratus de succo illarum recens presso. Hic Acetosae." (Procedure 7. A natural salt of plants prepared from their freshly pressed juice. This [salt obtained] from sorrel.)
Henry Enfield Roscoe and Carl Schorlemmer, ed.s, A Treatise on Chemistry (New York, New York: D. Appleton and Co., 1890), volume 3, part 2, p. 105.
See also Wikipedia's articles "Oxalis acetosella" and "Potassium hydrogen oxalate".
Jump up ^ See:
François Pierre Savary, Dissertatio Inauguralis De Sale Essentiali Acetosellæ [Inaugural dissertation on the essential salt of wood sorrel] (Jean François Le Roux, 1773). (in Latin) Savary noticed that when he distilled sorrel salt (potassium hydrogen oxalate), crystals would sublimate onto the receiver. From p. 17: "Unum adhuc circa liquorem acidum, quem sal acetosellae tam sincerissimum a nobis paratum quam venale destillatione fundit phoenomenon erit notandum, nimirum quod aliquid ejus sub forma sicca crystallina lateribus excipuli accrescat, ..." (One more [thing] will be noted regarding the acid liquid, which furnished for us sorrel salt as pure as commercial distillations, [it] produces a phenomenon, that evidently something in dry, crystalline form grows on the sides of the receiver, ...) These were crystals of oxalic acid.
Leopold Gmelin with Henry Watts, trans., Hand-book of Chemistry (London, England: Cavendish Society, 1855), volume 9, p. 111.
Jump up ^ See:
Torbern Bergman with Johan Afzelius (1776) Dissertatio chemica de acido sacchari [Chemical dissertation on sugar acid] (Uppsala, Sweden: Edman, 1776).
Torbern Bergman, Opuscula Physica et Chemica, (Leipzig (Lipsia), (Germany): I.G. Müller, 1776), volume 1, "VIII. De acido Sacchari," pp. 238-263.
Jump up ^ Carl Wilhelm Scheele (1784) "Om Rhabarber-jordens bestånds-delar, samt sått at tilreda Acetosell-syran" (On rhubarb-earth's constituents, as well as ways of preparing sorrel-acid), Kungliga Vetenskapsakademiens Nya Handlingar [New Proceedings of the Royal Academy of Science], 2nd series, 5 : 183-187. (in Swedish) From p. 187: "Således finnes just samma syra som vi genom konst af socker med tilhjelp af salpeter-syra tilreda, redan förut af naturen tilredd uti o̊rten Acetosella." (Thus it is concluded [that] the very same acid as we prepare artificially by means of sugar with the help of nitric acid, [was] previously prepared naturally in the herb acetosella [i.e., sorrel].)
Jump up ^ See:
F. Wöhler (1824) "Om några föreningar af Cyan" (On some compounds of cyanide), Kungliga Vetenskapsakademiens Handlingar [Proceedings of the Royal Academy of Science], pp. 328-333. (in Swedish)
Reprinted in German as: F. Wöhler (1825) "Ueber Cyan-Verbindungen" (On cyanide compounds), Annalen der Physik und Chemie, 2nd series, 3 : 177-182.
^ Jump up to: a b c d Wilhelm Riemenschneider, Minoru Tanifuji "Oxalic acid" in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi: 10.1002/14356007.a18_247.
Jump up ^ Eiichi, Yonemitsu; Tomiya, Isshiki; Tsuyoshi, Suzuki and Yukio, Yashima "Process for the production of oxalic acid", U.S. Patent 3,678,107, priority date March 15, 1969
Jump up ^ Von Wagner, Rudolf (1897). Manual of chemical technology. New York: D. Appleton & Co. p. 499.
Jump up ^ Practical Organic Chemistry by Julius B. Cohen, 1930 ed. preparation #42
Jump up ^ Clarke H. T.;. Davis, A. W. (1941). "Oxalic acid (anhydrous)". Organic Syntheses: 421. CS1 maint: Multiple names: authors list (link) ; Collective Volume, 1
Jump up ^ Bouwman, Elisabeth; Angamuthu, Raja; Byers, Philip; Lutz, Martin; Spek, Anthony L. (July 15, 2010). "Electrocatalytic CO2 Conversion to Oxalate by a Copper Complex" (Submitted manuscript). Science. 327 (5393): 313–315. doi:10.1126/science.1177981. PMID 20075248.
Jump up ^ Wells, A.F. (1984) Structural Inorganic Chemistry, Oxford: Clarendon Press. ISBN 0-19-855370-6.
Jump up ^ Bowden, E. (1943). "Methyl oxalate". Organic Syntheses: 414. ; Collective Volume, 2
Jump up ^ Kovacs K.A.; Grof P.; Burai L.; Riedel M. (2004). "Revising the mechanism of the permanganate/oxalate reaction". J. Phys. Chem. A. 108 (50): 11026–11031. doi:10.1021/jp047061u.
Jump up ^ Dutton, M. V.; Evans, C. S. (1996). "Oxalate production by fungi: Its role in pathogenicity and ecology in the soil environment". Canadian Journal of Microbiology. 42 (9): 881–895. doi:10.1139/m96-114. .
Jump up ^ Rombauer, Rombauer Becker, and Becker (1931/1997). Joy of Cooking, p.415. ISBN 0-684-81870-1.
Jump up ^ Attenborough, David. "Surviving." The Private Life of Plants: A Natural History of Plant Behaviour. Princeton, NJ: Princeton UP, 1995. 265+. "OpenLibrary.org: The Private Life of Plants" Print.
Jump up ^ Sabbioni, Cristina; Zappia, Giuseppe (2016). "Oxalate patinas on ancient monuments: The biological hypothesis". Aerobiologia. 7: 31–37. doi:10.1007/BF02450015.
Jump up ^ . doi:10.1007/978-3-642-27682-8_27-1 (inactive 2018-07-31). Missing or empty |title= (help)
Jump up ^ EPJ Web of Conferences
Jump up ^ Novoa, William; Alfred Winer; Andrew Glaid; George Schwert (1958). "Lactic Dehydrogenase V. inhibition by Oxamate and Oxalate". Journal of Biological Chemistry. 234 (5): 1143–8. PMID 13654335.
Jump up ^ Le, Anne; Charles Cooper; Arvin Gouw; Ramani Dinavahi; Anirban Maitra; Lorraine Deck; Robert Royer; David Vander Jagt; Gregg Semenza; Chi Dang (14 December 2009). "Inhibition of lactate dehydrogenase A induces oxidative stress and inhibits tumor progression". Proceedings of the National Academy of Sciences. 107 (5): 2037–2042. doi:10.1073/pnas.0914433107. PMC 2836706  . PMID 20133848.
Jump up ^ Exploring New Methods for Varroa Mite Control, Yu-Lun Lisa Fu
Jump up ^ Jackson, Faith. "Quartz Crystal Cleaning". bluemooncrystals.com
Jump up ^ "Rock Currier – Cleaning Quartz". mindat.org
Jump up ^ All data not specifically annotated is from Agriculture Handbook No. 8-11, Vegetables and Vegetable Products, 1984. ("Nutrient Data : Oxalic Acid Content of Selected Vegetables". ars.usda.gov)
Jump up ^ Pucher, GW; Wakeman, AJ; Vickery, HB (1938). "The organic acids of rhubarb (Rheum hybridium). III. The behavior of the organic acids during culture of excised leaves". Journal of Biological Chemistry. 126 (1): 43.
Jump up ^ Durham, Sharon. "Making Spinach with Low Oxalate Levels". AgResearch Magazine (January 2017). United States Department of Agriculture. Retrieved 26 June 2017. 'The scientists analyzed oxalate concentrations in 310 spinach varieties—300 USDA germplasm accessions and 10 commercial cultivars. “These spinach varieties and cultivars displayed oxalate concentrations from 647.2 to 1286.9 mg/100 g on a fresh weight basis,” says Mou.'
Jump up ^ Oxalic acid dihydrate. MSDS. sigmaaldrich.com
Jump up ^ "Oxalic Acid Material Safety Data Sheet" (PDF). Radiant Indus Chem. Retrieved 2014-05-20.
Jump up ^ "CDC – Immediately Dangerous to Life or Health Concentrations (IDLH): Oxalic acid – NIOSH Publications and Products". cdc.gov
Jump up ^ EMEA Committee for veterinary medicinal products, oxalic acid summary report, December 2003
External links[edit]
Wikimedia Commons has media related to Oxalic acid.
Oxalic acid MS Spectrum
International Chemical Safety Card 0529
NIOSH Guide to Chemical Hazards (CDC)
Table: Oxalic acid content of selected vegetables (USDA)
Alternative link: Table: Oxalic Acid Content of Selected Vegetables (USDA)
About rhubarb poisoning (The Rhubarb Compendium)
Oxalosis & Hyperoxaluria Foundation (OHF) The Oxalate Content of Food 2008 (PDF)
Oxalosis & Hyperoxaluria Foundation (OHF) Diet Information
Calculator: Water and solute activities in aqueous oxalic acid
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Linear saturated dicarboxylic acids (H2OC-R-CO2H)
Ethanedioic acid (Oxalic acid) C2H2O4
Propanedioic acid (Malonic acid) C3H4O4
Butandioic acid (Succinic acid) C4H6O4
Pentanedioic acid (Glutaric acid) C5H8O4
Hexanedioic acid (Adipic acid) C6H10O4
Heptanedioic acid (Pimelic acid) C7H12O4
Octanedioic acid (Suberic acid) C8H14O4
Nonanedioic acid (Azelaic acid) C9H16O4
Decanedioic acid (Sebacic acid) C10H18O4
Category:Dicarboxylic acids
Authority control
GND: 4173006-9
Retrieved from "https://en.wikipedia.org/w/index.php?title=Oxalic_acid&oldid=853582054"
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