3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid

• ChemBase ID: 5403
• Molecular Formular: C10H10O4
• Molecular Mass: 194.184
• Monoisotopic Mass: 194.0579088
• SMILES: c1(ccc(cc1OC)/C=C/C(=O)O)O
• Canonical SMILES: COc1cc(/C=C/C(=O)O)ccc1O
• InChI: InChI=1S/C10H10O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+
• InChIKey: KSEBMYQBYZTDHS-HWKANZROSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid; (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid
• IUPAC Traditional name: 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid; ferulic acid
• Synonyms: 3-[4-Hydroxy-3-methoxyphenyl]-2-propenoic Acid; 3-[4-Hydroxy-3-methoxyphenyl)acrylic Acid; 4'-Hydroxy-3'-(methoxy)cinnamic Acid; Ferulaic Acid; NSC 674320; trans-4-Hydroxy-3-methoxycinnamic acid; trans-Ferulic acid; 4-Hydroxy-3-methoxycinnamic acid; Ferulic acid; Fumalic acid; (2E)-3-(4-Hydroxy-3-methoxyphenyl)acrylic acid; 4-Hydroxy-3-methoxycinnamic acid; FERULIC ACID; 3-(4-HYDROXY-3-METHOXYPHENYL)-2-PROPENOIC ACID; trans-Ferulic acid; trans-4-Hydroxy-3-methoxycinnamic acid; (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid; 2-propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-; 3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid; 3-(4-hydroxy-3-methoxyphenyl)acrylic acid; 3-methoxy-4-hydroxycinnamic acid; (2E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid; Ferulate; Coniferic acid; (E)-ferulic acid; trans-4-Hydroxy-3-methoxycinnamic acid; Ferulic acid; 反式-4-羟基-3-甲氧基肉桂酸; 反式-4-羟基-3-甲氧基肉桂酸

Database IDs

• CAS Number: 537-73-5; 1135-24-6; 537-98-4
• EC Number: 208-679-7; 214-490-0
• MDL Number: MFCD00004400
• Beilstein Number: 1371483; 1570363
• Merck Index: 144062
• PubChem SID: 24847872; 160968832; 24870004; 99444238; 24902078
• PubChem CID: 445858
• CHEBI ID: 17620
• CHEMBL: 32749
• Chemspider ID: 393368
• DrugBank ID: DB07767
• Wikipedia Title: Ferulic_acid

CALCULATED PROPERTIES

JChem

• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.05890093
• LogD (pH = 7.4): -1.6033499
• Log P: 1.6748496
• Molar Refractivity: 51.504 cm^3
• Polarizability: 19.349815 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true
• Acid pKa: 3.7673485

ALOGPS 2.1

• Log P: 1.58
• LOG S: -2.33
• Solubility (Water): 9.06e-01 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; Ethyl Acetate; Methanol; Water
• Apperance: Crystalline Powder; Pale Yellow Solid; Powder
• Melting Point: 168°C; 168-171°C; 168-172 °C(lit.); 168–172 °C; 170-175°C; 171-175 °C; 172-174°C; 230°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer; Room Temperature (15-30°C)
• Storage Warning: IRRITANT; Irritant
• RTECS: GD9275000; UD3365500
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; R:36/37/38
• Safety Statements: 26-36; 26-37; S:20-25-26-37/39
• TSCA Listed: false; 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• NFPA704:
  

  1

  2

  0
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥99%; ≥99.0% (HPLC); 95+%; 97%; 98%; 99%
• Grade: certified reference material; matrix substance for MALDI-MS; puriss. p.a.; TraceCERT®
• Salt Data: Free Base
• Cation Traces: Ba: ≤5 mg/kg; Ca: ≤10 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
• Analyte suitability: peptides; proteins
• abs.: absorption/337 nm ≥2000 (mol. absorption)
• Appearance: slightly yellow powder
• Linear Formula: HOC6H3(OCH3)CH=CHCO2H
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 05213110

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02101685

Crystalline

DrugBank - DB07767

Drug information: experimental

Sigma Aldrich - W518301

Biochem/physiol Actions
Hydroxycinnamic acid found in plant-based foods. Antioxidant.
Packaging
1 kg in poly bottle
1 sample in glass bottle
100 g in poly bottle
5 kg in poly drum

Sigma Aldrich - 18077

Biochem/physiol Actions
Hydroxycinnamic acid found in plant-based foods. Antioxidant.

Sigma Aldrich - 128708

Biochem/physiol Actions
Hydroxycinnamic acid found in plant-based foods. Antioxidant.
Packaging
5, 25, 100 g in glass bottle

Sigma Aldrich - 46278

Biochem/physiol Actions
Hydroxycinnamic acid found in plant-based foods. Antioxidant.

Sigma Aldrich - 52229

Biochem/physiol Actions
Hydroxycinnamic acid found in plant-based foods. Antioxidant.
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

Selleck Chemicals - S2300

Research Area: Cardiovascular Disease , Neurological Disease
Biological Activity:
Fumalic acid(Ferulic acid) is a hydroxycinnamic acid and a type of organic compound found in the Ferula assafoetida L. or Ligusticum chuanxiong. It has many pharmacology functions, such as anti-blood platelet collection , ease pain better the alive of prostate , relax the blood vessel convulsion. Like many phenols, it is an antioxidant in the sense that it is reactive toward free radicals such as reactive oxygen species (ROS). ROS and free radicals are implicated in DNA damage, cancer, accelerated cell aging. Animal studies and in vitro studies suggest that ferulic acid may have direct antitumor activity against breast cancer and liver cancer. Ferulic acid may have pro-apoptotic effects in cancer cells, thereby leading to their destruction. Ferulic acid may be effective at preventing cancer induced by exposure to the carcinogenic compounds benzopyrene and 4-nitroquinoline 1-oxide. [1][2]

Toronto Research Chemicals - F308900

Widely distributed in small amounts in plants. Used as an antioxidant and food preservative.

REFERENCES

• Kampa M et al. Breast Cancer Res. 2004;6(2):R63-74.
• Smart, M.G., et al.: Aust. J. Plant Physiol., 6, 485 (1979)
• Chen, C., et al.: J. Food Lipids, 2, 35,1995, Benzie, I., et al.: Anal. Biochem. 239, 70 (1979)
• Nardini, M., et al.: Food Chem., 79, 119 (1979)
• Lee, J., et al.: J. Agric. Food Chem., 52, 2647