(2E)-but-2-enedioic acid

• ChemBase编号: 3907
• 分子式: C4H4O4
• 平均质量: 116.07216
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (2E)-but-2-enedioic acid; but-2-enedioic acid
• IUPAC传统名: fumaric acid; butenedioic acid
• 别名: 富马酸; 马来酸; 富马酸; 失水苹果酸; 顺丁烯二酸; 马来酸; 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

登记号

• CAS号: 110-17-8; 110-16-7
• EC号: 203-742-5; 203-743-0
• MDL号: MFCD00002700; MFCD00063177
• Beilstein号: 605763; 605762
• 默克索引号: 144287
• PubChem SID: 24845580; 24882462; 24900967; 46508977; 160967342; 24894967; 24854434
• PubChem CID: 444972
• CHEBI ID: 18012
• ATC码: D05AX01
• CHEMBL: 503160
• Chemspider ID: 10197150
• DrugBank ID: DB04299
• FEMA编号: 2488
• KEGG ID: C00122
• 美国药典/FDA物质标识码: 88XHZ13131
• 维基百科标题: Fumaric_acid
• 欧洲委员会编号: 25
• Flavis Number: 8.025
• E编码: E297

理论计算性质

JChem

• Acid pKa: 3.5457325
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): -3.1057482
• LogD (pH = 7.4): -6.3127127
• Log P: -0.04091433
• 摩尔折射率: 24.607 cm^3
• 极化性: 9.126 Å^3
• 极化表面积: 74.6 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.21
• LOG S: -0.68
• 溶解度: 2.41e+01 g/l

分子性质

理化性质

• 溶解度: 0.63 g/100 mL in water; DMSO
• 外观: Powder; White solid; White Solid
• 熔点: 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.
• 沸点: 290°C; ca. 100 °C
• 闪点: 127 °C; 230 °C; 260.6 °F; 273 °C (open cup); 273°C(523°F); 446 °F
• 自燃点: 1364 °F; 740°C
• 密度: 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
• 蒸汽压: < .001 hPa at 20 °C; 1.7 mmHg ( 165 °C); 30 hPa at 20 °C
• pKa: pk_a1 = 3.03, pk_a2 = 4.44
• 感官: sour

安全信息

• 保存条件: Refrigerator; Room Temperature (15-30°C)
• 保存注意事项: Harmful/Irritant
• RTECS编号: LS9625000; OM9625000
• 欧盟危险性物质标志: 环境危害性(Nature polluting) (N); 刺激性(Irritant) (Xi); 有害性(Harmful) (Xn)
• 联合国危险货物编号: 2215; 3077
• 德国WGK号: 1
• 联合国危险货物等级: 8; 9
• 联合国危险货物包装类别(PG): III
• 澳大利亚Hazchem: 2X
• 危险公开号: 22-36/37/38-43; 36; R:22-36/37/38; R:36; R:36-58; R36
• 安全公开号: 24-26-28-37-46; 26; S:26; S:26-28-37; S:26-61; S2 S26
• 欧盟危险货物分类: C10; M7
• 欧盟危险识别号(EUHIN): 13; 8B
• 美国ERG指导号: 156; 171
• TSCA收录: 是
• GHS危险品标识: GHS05; GHS07
• GHS警示词: Danger; Warning
• NFPA704:
  

  1

  2

  0
• 爆炸极限: 40 %
• GHS危险声明: H302 + H312-H315-H317-H318-H319-H335; H319
• GHS警示性声明: P261-P280-P305 + P351 + P338; P305 + P351 + P338; P305+P351+P338
• 个人保护装置: 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)

药理学性质

• 过敏源: no known allergens

产品相关信息

• 纯度: ≥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)
• 级别: FG; Kosher; NI; Ph Eur; puriss.; purum; REAGENT; SAJ special grade; TECHNICAL; TraceCERT®; USP/NF
• 适用性: suitable for cell culture
• 燃烧残渣: ≤0.1%
• 简要说明: qNMR Standard for D2O and organic solvents (6.2 ppm)
• 杂质: ≤0.1 % (w/w) organic impurities (maleic acid) (HPLC); ≤0.5% water (Karl Fischer); ≤10 ppm heavy metals
• 有效期: (limited shelf life, expiry date on the label)
• 产品质量级别: GMP
• 药典: testing & handling conforms to Pharmacopeia
• 线性分子式: HO2CCH=CHCO2H; HOOCCH=CHCOOH

详细说明

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

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

Sigma Aldrich - 92816

Analysis Note
此认证标准物质 (CRM) 的生产和认证都符合 ISO/IEC 17025 和 ISO Guide 34 的要求。此 CRM 可溯源到 NIST SRM。
General description
认证的含量经定量 NMR 确定，并且证书上标明不确定度和有效期。 证书下载：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
法律信息
TraceCERT 注册商标 Sigma-Aldrich Co. LLC
Protocols & Applications
Certified Standards for Quantitative 1H-NMR (qNMR)

Sigma Aldrich - F19353

包装
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
在 165°C 的温度和 1.7mmHg 的压力（文献值）下升华

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.
法律信息
TraceCERT 注册商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - 47910

Analysis Note
在 165°C 的温度和 1.7mmHg 的压力（文献值）下升华

Sigma Aldrich - W248800

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

Sigma Aldrich - 240745

包装
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.

参考文献

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