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

• ChemBase ID: 1649
• Molecular Formular: C9H8O4
• Molecular Mass: 180.15742
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid; 3-(3,4-dihydroxyphenyl)prop-2-enoic acid
• IUPAC Traditional name: caffeic acid; 3,4-dihydroxycinnamic acid; caffeyl alcohol; (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
• Synonyms: 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; 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

Database IDs

• CAS Number: 3598-26-3; 331-39-5; 501-16-6
• EC Number: 206-361-2
• MDL Number: MFCD00004392
• Beilstein Number: 2210883; 1954563
• Merck Index: 141635
• PubChem SID: 46504491; 24881777; 160965106; 24881776; 24278290
• PubChem CID: 2518; 689043
• CHEBI ID: 36281; 16433
• CHEMBL: 145
• Chemspider ID: 600426; 2423
• DrugBank ID: DB01880
• KEGG ID: C01481
• Unique Ingredient Identifier: U2S3A33KVM
• Wikipedia Title: Caffeyl_alcohol; Caffeic_acid

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.64384
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -0.32416362
• LogD (pH = 7.4): -1.8039718
• Log P: 1.5289556
• Molar Refractivity: 47.0217 cm^3
• Polarizability: 17.452097 Å^3
• Polar Surface Area: 77.76 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.67
• LOG S: -2.05
• Solubility (Water): 1.61e+00 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; ethanol: soluble50 mg/mL; Methanol; moderate in water
• Apperance: light beige powder; Pale yellow to Tan Solid; powder; Powder; slightly beige powder; White solid
• Melting Point: 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.
• Density: 1.478 g/cm3
• Absorption Wavelength: 327 nm and a shoulder at c. 295 nm in acidified methanol
• Hydrophobicity(logP): 0.975; 1.15 [SANGSTER (1993)]

Safety Information

• Storage Condition: -20°C; Hygroscopic, Refrigerator, Under Inert Atmosphere; Room Temperature (15-30°C)
• Storage Warning: Carcinogenic/Harmful/Irritant
• RTECS: GD8950000
• European Hazard Symbols: Toxic (T); X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 36/37/38-40; 36-40; 63-36/37/38-40-68; R:45
• Safety Statements: 26-36/37; 26-36/37/39; S:28-36/37/39-45-53
• TSCA Listed: 否
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• NFPA704:
  

  1

  1

  0
• GHS Hazard statements: H315-H319-H335-H351-H361; H319-H351; H351-H315-H319-H335
• GHS Precautionary statements: P261-P281-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A; P281-P305 + P351 + P338
• Personal Protective Equipment: 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

Pharmacology Properties

• Gene Information: human ... ELA2(1991)rat ... Alox5(25290)
• Mechanism of Action: Carcinogenic inhibitor

Product Information

• Purity: ≥95.0% (HPLC); ≥98.0% (HPLC); ≥99.0% (HPLC); 95%; 99%
• Grade: certified reference material; matrix substance for MALDI-MS; puriss. p.a.; purum; TraceCERT®
• Salt Data: Free Base
• Suitability: in accordance for UV test
• Cation Traces: 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
• Biological Source: Widespread in plants, free and as glycosides. Found by Bate-Smith in 66% of investigated dicotyledonous and 50% of investigated monocotyledonous plant spp.
• Shelf Life: (limited shelf life, expiry date on the label)
• Application(s): Anti-HIV; Antineoplastic agent; Antioxidant; Choleretic and hepatotropic activity
• Analyte suitability: peptides; proteins
• Linear Formula: (HO)2C6H3CH=CHCO2H
• Empirical Formula (Hill Notation): C9H8O4

DETAILS

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
A natural dietary phenolic compound found in plants that is an anti-oxidant. Inhibits the synthesis of leukotrienes that are involved in immunoregulation, inflammation and allergy. Inhibits Cu2+-induced LDL oxidation.

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
Inhibits 5-lipoxygenase activity in mastocyma cells1
Biochem/physiol Actions
A natural dietary phenolic compound found in plants that is an anti-oxidant. Inhibits the synthesis of leukotrienes that are involved in immunoregulation, inflammation and allergy. Inhibits Cu2+-induced LDL oxidation.

Sigma Aldrich - 60018

Biochem/physiol Actions
A natural dietary phenolic compound found in plants that is an anti-oxidant. Inhibits the synthesis of leukotrienes that are involved in immunoregulation, inflammation and allergy. Inhibits Cu2+-induced LDL oxidation.

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.
Legal Information
TraceCERT is a registered trademark of 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

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