(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid

• ChemBase编号: 1649
• 分子式: C9H8O4
• 平均质量: 180.15742
• 单一同位素质量: 180.04225874
• SMILES: C(=O)(/C=C/c1cc(c(cc1)O)O)O
• Canonical SMILES: OC(=O)/C=C/c1ccc(c(c1)O)O
• InChI: InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+
• InChIKey: QAIPRVGONGVQAS-DUXPYHPUSA-N

名称和登记号

名称

• IUPAC标准名: (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid; 3-(3,4-dihydroxyphenyl)prop-2-enoic acid
• IUPAC传统名: caffeic acid; 3,4-dihydroxycinnamic acid; caffeyl alcohol; (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
• 别名: 3,4-二羟基肉桂酸; 咖啡酸; 3,4-二羟基肉桂酸, 主体成分为反式; 3-(3,4-Dihydroxyphenyl)-2-propenoic Acid; 3,4-Dihydroxybenzeneacrylic Acid; 4-(2-Carboxyethenyl)-1,2-dihydroxybenzene; NSC 57197; NSC 623438; (E)-3-(3,4-dihydroxyphenyl)acrylic acid; 3,4-Dihydroxycinnamic acid; Caffeic acid; 3,4-Dihydroxycinnamic Acid; Caffeic acid; Caffeic acid; 3-(3,4-Dihydroxyphenyl)prop-2-enoic acid; 3-(3,4-Dihydroxyphenyl)acrylic acid; Caffeyl alcohol; Caffeoyl alcohol; 3,4-Dihydroxycinnamyl alcohol; Caffeyl alcohol; trans-3,4-Dihydroxycinnamic acid; trans-Caffeic acid; 3-(3,4-dihydroxyphenyl)prop-2-enoic acid; 3,4-Dihydroxycinnamic acid, predominantly trans

登记号

• CAS号: 501-16-6; 3598-26-3; 331-39-5
• EC号: 206-361-2
• MDL号: MFCD00004392
• Beilstein号: 1954563; 2210883
• 默克索引号: 141635
• PubChem SID: 24881776; 24278290; 24881777; 160965106; 46504491
• PubChem CID: 689043; 2518
• CHEBI ID: 36281; 16433
• CHEMBL: 145
• Chemspider ID: 2423; 600426
• DrugBank ID: DB01880
• KEGG ID: C01481
• 美国药典/FDA物质标识码: U2S3A33KVM
• 维基百科标题: Caffeyl_alcohol; Caffeic_acid

理论计算性质

JChem

• Acid pKa: 3.64384
• 质子受体: 4
• 质子供体: 3
• LogD (pH = 5.5): -0.32416362
• LogD (pH = 7.4): -1.8039718
• Log P: 1.5289556
• 摩尔折射率: 47.0217 cm^3
• 极化性: 17.452097 Å^3
• 极化表面积: 77.76 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: 1.67
• LOG S: -2.05
• 溶解度: 1.61e+00 g/l

分子性质

理化性质

• 溶解度: DMSO; ethanol: soluble50 mg/mL; Methanol; moderate in water
• 外观: light beige powder; Pale yellow to Tan Solid; powder; Powder; slightly beige powder; White solid
• 熔点: 144-5°C; 193-196°C; 194-198°C; 194-198°C (dec.); 211 - 213°C; 211-213 °C (dec.)(lit.); 223–225 °C; ca 202°C dec.
• 密度: 1.478 g/cm3
• 紫外吸收波长: 327 nm and a shoulder at c. 295 nm in acidified methanol
• 疏水性(logP): 0.975; 1.15 [SANGSTER (1993)]

安全信息

• 保存条件: -20°C; Hygroscopic, Refrigerator, Under Inert Atmosphere; Room Temperature (15-30°C)
• 保存注意事项: Carcinogenic/Harmful/Irritant
• RTECS编号: GD8950000
• 欧盟危险性物质标志: 有毒(Toxic) (T); X; 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 36/37/38-40; 36-40; 63-36/37/38-40-68; R:45
• 安全公开号: 26-36/37; 26-36/37/39; S:28-36/37/39-45-53
• TSCA收录: 否
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Warning
• NFPA704:
  

  1

  1

  0
• GHS危险声明: H315-H319-H335-H351-H361; H319-H351; H351-H315-H319-H335
• GHS警示性声明: P261-P281-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A; P281-P305 + P351 + P338
• 个人保护装置: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

药理学性质

• 相关基因信息: human ... ELA2(1991)rat ... Alox5(25290)
• 生物活性机理: Carcinogenic inhibitor

产品相关信息

• 纯度: ≥95.0% (HPLC); ≥98.0% (HPLC); ≥99.0% (HPLC); 95%; 99%
• 级别: certified reference material; matrix substance for MALDI-MS; puriss. p.a.; purum; TraceCERT®
• 成盐信息: Free Base
• 适用性: in accordance for UV test
• 痕量阳离子: Ba: ≤5 mg/kg; Ca: ≤10 mg/kg; Ca: ≤20 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤20 mg/kg; K: ≤50 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Na: ≤50 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Zn: ≤5 mg/kg
• 生物来源: Widespread in plants, free and as glycosides. Found by Bate-Smith in 66% of investigated dicotyledonous and 50% of investigated monocotyledonous plant spp.
• 有效期: (limited shelf life, expiry date on the label)
• 应用领域: Anti-HIV; Antineoplastic agent; Antioxidant; Choleretic and hepatotropic activity
• 适用分析物: peptides; proteins
• 线性分子式: (HO)2C6H3CH=CHCO2H
• Empirical Formula (Hill Notation): C9H8O4

详细说明

MP Biomedicals - 02104797

Yellowish-brown crystals

MP Biomedicals - 05209770

MP Biomedicals Rare Chemical collection

DrugBank - DB01880

Drug information: experimental

Selleck Chemicals - S2277

Research Area: Cancer
Biological Activity:
Caffeic acid is a hydroxycinnamic acid, a naturally occurring organic compound.It has been shown to inhibit carcinogenesis, although other experiments show possible carcinogenic effects. It is also known as an antioxidant in vitro and also in vivo. Caffeic acid also shows immunomodulatory and antiinflammtory activity. Caffeic acid outperformed the other antioxidants, reducing aflatoxin production by more than 95 percent. The studies are the first to show that oxidative stress that would otherwise trigger or enhance Aspergillus flavus aflatoxin production can be stymied by caffeic acid. This opens the door to using natural anti-fungicide methods by supplementing trees with antioxidants. [1][2]

Sigma Aldrich - 06773

Biochem/physiol Actions
在植物中发现的抗氧化天然膳食酚类化合物。抑制在免疫调节、炎症和过敏中涉及到的白三烯的合成。也可抑制 Cu2+ 诱导的 LDL 氧化。

Sigma Aldrich - C0625

包装
2, 5, 25 g in poly bottle
Biochem/physiol Actions
在植物中发现的抗氧化天然膳食酚类化合物。抑制在免疫调节、炎症和过敏中涉及到的白三烯的合成。也可抑制 Cu2+ 诱导的 LDL 氧化。

Sigma Aldrich - 60020

Other Notes
可抑制肥大细胞瘤细胞中 5-脂氧合酶的活性1
Biochem/physiol Actions
在植物中发现的抗氧化天然膳食酚类化合物。抑制在免疫调节、炎症和过敏中涉及到的白三烯的合成。也可抑制 Cu2+ 诱导的 LDL 氧化。

Sigma Aldrich - 60018

Biochem/physiol Actions
在植物中发现的抗氧化天然膳食酚类化合物。抑制在免疫调节、炎症和过敏中涉及到的白三烯的合成。也可抑制 Cu2+ 诱导的 LDL 氧化。

Sigma Aldrich - 51868

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

Toronto Research Chemicals - C080000

Caffeic Acid is a constituent of plants, probably occurs in plants only in conjugated forms. Caffeic acid is found in all plants because it is a key intermediate in the biosynthesis of lignin, one of the principal sources of biomass. Caffeic acid is one o

参考文献

• Olthof MR et al. J Nutr. 2001 Jan;131(1):66-71.
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• IARC Monog., 1993, 56, 115, (Caffeic acid, rev, tox)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CAK375