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537-73-5 molecular structure
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3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid

ChemBase ID: 5403
Molecular Formular: C10H10O4
Molecular Mass: 194.184
Monoisotopic Mass: 194.0579088
SMILES and InChIs

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

Cite this record

CBID:5403 http://www.chembase.cn/molecule-5403.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

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

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) -0.05890093  LogD (pH = 7.4) -1.6033499 
Log P 1.6748496  Molar Refractivity 51.504 cm3
Polarizability 19.349815 Å3 Polar Surface Area 66.76 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Acid pKa 3.7673485 
Log P 1.58  LOG S -2.33 
Solubility (Water) 9.06e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Ethyl Acetate expand Show data source
Methanol expand Show data source
Water expand Show data source
Apperance
Crystalline Powder expand Show data source
Pale Yellow Solid expand Show data source
Powder expand Show data source
Melting Point
168°C expand Show data source
168-171°C expand Show data source
168-172 °C(lit.) expand Show data source
168–172 °C expand Show data source
170-175°C expand Show data source
171-175 °C expand Show data source
172-174°C expand Show data source
230°C expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
Room Temperature (15-30°C) expand Show data source
Storage Warning
IRRITANT expand Show data source
Irritant expand Show data source
RTECS
GD9275000 expand Show data source
UD3365500 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
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German water hazard class
3 expand Show data source
Risk Statements
36/37/38 expand Show data source
R:36/37/38 expand Show data source
Safety Statements
26-36 expand Show data source
26-37 expand Show data source
S:20-25-26-37/39 expand Show data source
TSCA Listed
false expand Show data source
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
NFPA704
NFPA 704 diagram
1
2
0
expand Show data source
GHS Hazard statements
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
P261-P305+P351+P338-P302+P352-P321-P405-P501A expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Purity
≥99% expand Show data source
≥99.0% (HPLC) expand Show data source
95+% expand Show data source
97% expand Show data source
98% expand Show data source
99% expand Show data source
Grade
certified reference material expand Show data source
matrix substance for MALDI-MS expand Show data source
puriss. p.a. expand Show data source
TraceCERT® expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Cation Traces
Ba: ≤5 mg/kg expand Show data source
Ca: ≤10 mg/kg expand Show data source
Cd: ≤5 mg/kg expand Show data source
Co: ≤5 mg/kg expand Show data source
Cr: ≤5 mg/kg expand Show data source
Cu: ≤5 mg/kg expand Show data source
Fe: ≤20 mg/kg expand Show data source
K: ≤50 mg/kg expand Show data source
Mg: ≤5 mg/kg expand Show data source
Mn: ≤5 mg/kg expand Show data source
Na: ≤50 mg/kg expand Show data source
Ni: ≤5 mg/kg expand Show data source
Pb: ≤5 mg/kg expand Show data source
Zn: ≤5 mg/kg expand Show data source
Analyte suitability
peptides expand Show data source
proteins expand Show data source
abs.
absorption/337 nm ≥2000 (mol. absorption) expand Show data source
Appearance
slightly yellow powder expand Show data source
Linear Formula
HOC6H3(OCH3)CH=CHCO2H expand Show data source
Classification
Genuine Natural Compounds expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 05213110 external link
MP Biomedicals Rare Chemical collection
MP Biomedicals - 02101685 external link
Crystalline
DrugBank - DB07767 external link
Drug information: experimental
Selleck Chemicals - S2300 external link
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]
Sigma Aldrich - W518301 external link
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 - 128708 external link
Biochem/physiol Actions
Hydroxycinnamic acid found in plant-based foods. Antioxidant.
Packaging
5, 25, 100 g in glass bottle
Sigma Aldrich - 18077 external link
Biochem/physiol Actions
Hydroxycinnamic acid found in plant-based foods. Antioxidant.
Sigma Aldrich - 52229 external link
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
Sigma Aldrich - 46278 external link
Biochem/physiol Actions
Hydroxycinnamic acid found in plant-based foods. Antioxidant.
Toronto Research Chemicals - F308900 external link
Widely distributed in small amounts in plants. Used as an antioxidant and food preservative.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
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PATENTS

PATENTS

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INTERNET

INTERNET

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