(2E)-but-2-enedioic acid

• ChemBase ID: 3907
• Molecular Formular: C4H4O4
• Molecular Mass: 116.07216
• Monoisotopic Mass: 116.01095861
• SMILES: OC(=O)/C=C/C(=O)O
• Canonical SMILES: OC(=O)/C=C/C(=O)O
• InChI: InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+
• InChIKey: VZCYOOQTPOCHFL-OWOJBTEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-but-2-enedioic acid; but-2-enedioic acid
• IUPAC Traditional name: fumaric acid; butenedioic acid
• Synonyms: Allomaleic acid; trans-Butenedioic acid; Lichenic Acid; FUMARIC ACID; cis-1,2-Ethylenedicarboxylic Acid; Maleinic Acid; MALEIC ACID REAGENT GRADE; cis-Butenedioic acid; Toxilic acid; MALEIC ACID TECHNICAL GRADE; Fumaric acid; Acidum maleicum; (2E)-2-Butenedioic Acid; (2E)-But-2-enedioic Acid; (E)-2-Butenedioic Acid; 2-(E)-Butenedioic Acid; (E)-Butenedioic Acid; Bakeshure 451; Bakeshure 470; FC 33; NSC 2752; Petrom; trans-1,2-Ethylenedicarboxylic Acid; trans-2-Butenedioic Acid; Maleic Acid; (2Z)-But-2-ene-1,4-dioic acid; trans-1,2-Ethylenedicarboxylic acid; 2-Butenedioic acid; trans-butenedioic acid; Boletic acid; Donitic acid; FUMARIC ACID FREE ACID; Acidum fumaricum; Maleic acid; 富马酸; 马来酸; 富马酸; 失水苹果酸; 顺丁烯二酸; 马来酸

Database IDs

• CAS Number: 110-17-8; 110-16-7
• EC Number: 203-742-5; 203-743-0
• MDL Number: MFCD00002700; MFCD00063177
• Beilstein Number: 605762; 605763
• Merck Index: 144287
• PubChem SID: 24845580; 24882462; 46508977; 160967342; 24894967; 24854434; 24900967
• PubChem CID: 444972
• CHEBI ID: 18012
• ATC CODE: D05AX01
• CHEMBL: 503160
• Chemspider ID: 10197150
• DrugBank ID: DB04299
• FEMA ID: 2488
• KEGG ID: C00122
• Unique Ingredient Identifier: 88XHZ13131
• Wikipedia Title: Fumaric_acid
• Council of Europe Number: 25
• Flavis Number: 8.025
• E Number: E297

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.5457325
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -3.1057482
• LogD (pH = 7.4): -6.3127127
• Log P: -0.04091433
• Molar Refractivity: 24.607 cm^3
• Polarizability: 9.126 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.21
• LOG S: -0.68
• Solubility (Water): 2.41e+01 g/l

PROPERTIES

Physical Property

• Solubility: 0.63 g/100 mL in water; DMSO
• Apperance: Powder; White solid; White Solid
• Melting Point: 130 - 130.5 °C; 137-140 °C; 137-140 °C(lit.); 287 °C; 287°C (sublimes); 296-299°C; 298-300 °C (subl.)(lit.); 299-300°C (sublimes); ca 299°C subl.
• Boiling Point: 290°C; ca. 100 °C
• Flash Point: 127 °C; 230 °C; 260.6 °F; 273 °C (open cup); 273°C(523°F); 446 °F
• Auto Ignition Point: 1364 °F; 740°C
• Density: 1.59 g/cm^3 at 20 °C; 1.59 g/mL at 25 °C(lit.); 1.625; 1.63 g/cm^3 at 20 °C; 1.63 g/ml; 1.635 g/cm3, solid
• Vapor Pressure: < .001 hPa at 20 °C; 1.7 mmHg ( 165 °C); 30 hPa at 20 °C
• pKa: pk_a1 = 3.03, pk_a2 = 4.44
• Organoleptic: sour

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• Storage Warning: Harmful/Irritant
• RTECS: LS9625000; OM9625000
• European Hazard Symbols: Nature polluting (N); Irritant (Xi); Harmful (Xn)
• UN Number: 2215; 3077
• German water hazard class: 1
• Hazard Class: 8; 9
• Packing Group: III
• Australian Hazchem: 2X
• Risk Statements: 22-36/37/38-43; 36; R:22-36/37/38; R:36; R:36-58; R36
• Safety Statements: 24-26-28-37-46; 26; S:26; S:26-28-37; S:26-61; S2 S26
• EU Classification: C10; M7
• EU Hazard Identification Number: 13; 8B
• Emergency Response Guidebook(ERG) Number: 156; 171
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger; Warning
• NFPA704:
  

  1

  2

  0
• Explode Limits: 40 %
• GHS Hazard statements: H302 + H312-H315-H317-H318-H319-H335; H319
• GHS Precautionary statements: P261-P280-P305 + P351 + P338; P305 + P351 + P338; P305+P351+P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves; dust mask type N95 (US), Eyeshields, Gloves
• Regulation Compliance: EU Regulation 1334/2008 & 178/2002; FCC; FDA 21 CFR (172.350); FDA 21 CFR (175.105); FDA 21 CFR (175.300); FDA 21 CFR (175.320); FDA 21 CFR (176.170)

Pharmacology Properties

• Allergens: no known allergens

Product Information

• Purity: ≥98.0% (HPLC); ≥99%; ≥99.0%; ≥99.0% (HPLC); ≥99.0% (T); ≥99.5% (T); 95+%; 99%; 99.5-100.5% (w/w) (calc.on dry substance, T)
• Grade: FG; Kosher; NI; Ph Eur; puriss.; purum; REAGENT; SAJ special grade; TECHNICAL; TraceCERT®; USP/NF
• Suitability: suitable for cell culture
• Ignition Residue: ≤0.1%
• Description: qNMR Standard for D2O and organic solvents (6.2 ppm)
• Impurities: ≤0.1 % (w/w) organic impurities (maleic acid) (HPLC); ≤0.5% water (Karl Fischer); ≤10 ppm heavy metals
• Shelf Life: (limited shelf life, expiry date on the label)
• Quality Level: GMP
• Pharmacopeia: testing & handling conforms to Pharmacopeia
• Linear Formula: HO2CCH=CHCO2H; HOOCCH=CHCOOH

DETAILS

MP Biomedicals - 02102233

Reagent Grade
Crystalline
Low fumaric acid content

MP Biomedicals - 02101742

Free Acid
Crystalline
Purity: 99%

MP Biomedicals - 05210837

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02102232

Technical Grade

MP Biomedicals - 02194668

Cell Culture Reagent
Free Acid
Purity: 99%

DrugBank - DB04299

Drug information: experimental

Sigma Aldrich - M153

Packaging
1 kg in poly bottle
100 g in poly bottle
5 g in glass bottle

Sigma Aldrich - 92816

Analysis Note
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34. This CRM is traceable to NIST SRM.
General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
Other Notes
Chemcial Shift: 6.2 ppm (chemical shifts may slightly vary depending on the experimental conditions)Suitable NMR solvents: D2O, MeOD, DMSO-d6
Legal Information
TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC
Protocols & Applications
Certified Standards for Quantitative 1H-NMR (qNMR)

Sigma Aldrich - F19353

Packaging
1, 3 kg in poly bottle
25 g in poly bottle

Sigma Aldrich - F8509

Application
TCA（三羧酸循环）分子，用作昆虫和哺乳动物细胞培养中的补充剂。

Sigma Aldrich - 47900

Analysis Note
sublimes at 165°C at 1.7 mm pressure (Lit.)

Sigma Aldrich - 76635

General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
Legal Information
TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 47910

Analysis Note
sublimes at 165°C at 1.7 mm pressure (Lit.)

Sigma Aldrich - W248800

Packaging
1 kg in poly bottle
1 sample in glass bottle
10, 25 kg in fiber drum

Sigma Aldrich - 240745

Packaging
1 kg in poly bottle
100 g in poly bottle
5 g in glass bottle

Toronto Research Chemicals - F500380

Occurs in many plants. Essential to vegetable and tissue respiration. Used as an antioxidant.

REFERENCES

• Jelitto, T., et al.: Planta, 188, 238 (1992)
• Son, H., et al.: J. Agric. Food Chem., 56, 8007 ( 2008),