Basic information
- CAS
3943-97-3- Standard SMILES
COC(=O)C=Cc1ccc(O)cc1- InChIKey
NITWSHWHQAQBAW-UHFFFAOYSA-N- Molecular formula
- C10H10O3
- Average molar mass
- 178.18 g/mol
- Monoisotopic mass
- 178.06299418
Overview
methyl hydroxycinnamate has been reported in Alpinia blepharocalyx, Gmelina asiatica, and other organisms with data available.
Names & identifiers
- Preferred name
- Methyl p-coumarate
- IUPAC
- methyl 3-(4-hydroxyphenyl)prop-2-enoate
- English name
- Methyl p-coumarate
- Molecular formula
- C10H10O3
- Molecular weight
- 178.18
Names & synonyms
3943-97-3methyl 3-(4-hydroxyphenyl)prop-2-enoateP9G2H2437Dp-Hydroxycinnamic acid methyl esterDTXSID1013158774-Coumaric acid methyl esterNSC-154578RefChem:925733para-coumaric acid methyl esterDTXCID801745760223-531-1CHEBI:86904
Show more names
METHYL COUMARATEmethyl (E)-3-(4-hydroxyphenyl)acrylateMethyl (2E)-3-(4-hydroxyphenyl)-2-propenoateTIMTEC-BB SBB002393METHYLPARA-COUMARATEp-Coumaric acid methyl4-coumaricacidmethylesterMETHYL P-HYDROXYCINNAMATE
Methyl 3-(4-Hydroxyphenyl)Acrylatemethyl 4-coumarateMethyl p-coumaratep-coumaric acid methyl ester2-Propenoic acid, 3-(4-hydroxyphenyl)-, methyl ester3-(4-Hydroxyphenyl)-2-propenoic Acid Methyl EsterNSC 154578trans-4-Hydroxycinnamic Acid Methyl Ester
Database identifiers
- CAS
3943-97-3- PubChem CID
- 92203
- DTXSID
DTXSID101315877- UNII
- P9G2H2437D
- EC Number
- 223-531-1
Properties
Computed structural properties
- XLogP
- 2.3
- Topological polar surface area
- 46.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 190
Physicochemical properties
- Melting point
- 144 · 144-145°
- Boiling point
- 306.6 · 306.6±17.0 °C(Predicted)
- Density
- 1 · 1+-.0.06 g/cm3(Predicted)
- vapor pressure
- 0.056 Pa · 0.056Pa at 25℃
- storage temp.
- Inert atmosphere,Room Temperature
- pka
- 8.82 · 8.82±0.13(Predicted)
- form
- crystals
- color
- White
- Water Solubility
- 5.332 g/L · 5.332g/L at 25℃
- InChI
- InChI=1S/C10H10O3/c1-13-10(12)7-4-8-2-5-9(11)6-3-8/h2-7,11H,1H3
- InChIKey
- NITWSHWHQAQBAW-UHFFFAOYSA-N
- SMILES
- C(OC)(=O)C=CC1=CC=C(O)C=C1
- LogP
- 1.88 at · 1.88 at 25℃
- CAS DataBase Reference
- 3943 · 3943-97-3(CAS DataBase Reference)
- FDA UNII
- 9 G2H2437D · P9G2H2437D
- NIST Chemistry Reference
- 2 · 2-Propenoic acid, 3-(4-hydroxyphenyl)-, methyl ester(3943-97-3)
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319
- Precautionary statements
- 261 · P261-P302+P352-P305+P351+P338
- HazardClass
- IRRITANT
- HS Code
- 2916399090 · 2916399090
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Warning
H317 (98.2%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P261, P272, P273, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 111 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 2-Propenoic acid, 3-(4-hydroxyphenyl)-, methyl ester
Status: Active Update: 12-06-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/18456
Hazard Classes and CategoriesSkin Sens. 1 (98.2%)
Safety data
- hs_code
- 2916399090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_class
- IRRITANT
- Hazard statements
- H302-H315-H319
- REACH Registrations
- Active
- Precautionary statements
- P261-P302+P352-P305+P351+P338
Chemistry & industry
Applications
DescriptionMethyl 4-hydroxycinnamate is an atifungal agent and a cinnamic acid derivative used in structure-antifungal activity relationship studies against Aspergillus flavus, Aspergillus terreus, and Aspergillus niger.
OccurrenceMethyl 4-hydroxycinnamate isolated from the herbs of Piper longum, Alpinia blepharocalyx, and Grevillea robusta.
Uses3-(4-Hydroxyphenyl)-2-propenoic Acid Methyl Ester is used in the synthesis of AB3 and constitutional isomeric AB2 phenylpropyl ether-based supramolecular dendrimers. Also used in the synthesis of potent antagonists of leukotrines.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers101 total
南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
阿诺西（上海）生物技术有限公司400-1107768 15058188853 · [email protected]
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安耐吉化学&3A（安徽泽升科技股份有限公司）400-0056266 · [email protected]
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Additional notes
DefinitionChEBI: 4-coumaric acid methyl ester is a cinnamate ester that is the methyl ester of 4-coumaric acid. It has a role as a melanin synthesis inhibitor, a fungal metabolite, an anti-inflammatory agent, an antifungal agent and a plant metabolite. It is a cinnamate ester, a member of phenols and a methyl ester. It derives from a 4-coumaric acid.
Related reactions
29 records
Compound notes
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