Methyl Cinnamate

HCID 637520
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Basic information

CAS
103-26-4
Standard SMILES
COC(=O)/C=C/c1ccccc1
InChIKey
CCRCUPLGCSFEDV-BQYQJAHWSA-N
Molecular formula
C10H10O2
Average molar mass
162.18 g/mol
Monoisotopic mass
162.06807956

Overview

Methyl cinnamate is a methyl ester resulting from the formal condensation of methyl cinnamic acid with methanol. It is found naturally in the essential oils of Alpinia and Basil leaf oil, and widely used in the flavor and perfume industries. It has a role as an insect attractant, a volatile oil component, a flavouring agent, a fragrance and an anti-inflammatory agent. It is an alkyl cinnamate and a methyl ester.

Names & identifiers

Preferred name
Methyl Cinnamate
IUPAC
methyl (E)-3-phenylprop-2-enoate
English name
Methyl cinnamate
Molecular formula
C10H10O2
Molecular weight
162.19

Names & synonyms

Methyl cinnamate103-26-4Cinnamic acid methyl esterMethyl (E)-3-phenylprop-2-enoateMethyl cinnamylateFEMA No. 2698CINNAMIC ACID, METHYL ESTERSemaSORB 9815533CV2ZCQLNSC-9411DTXCID5028118DTXSID6042151
Show more names
trans-Methyl Cinnamate2-Propenoic acid, 3-phenyl-, methyl ester, (E)-(E)-Methyl cinnamateMethyl cinnamate, (E)METHYL TRANS-3-PHENYLPROPENOATE(E)-3-Phenyl-2-propenoic acid methyl ester
RefChem:817677203-093-8Methyl trans-cinnamateMethyl (E)-cinnamate1754-62-7Methyl 3-phenylpropenoateMethyl 3-phenylacrylateMethylcinnamate

Database identifiers

CAS
103-26-4、1754-62-7
PubChem CID
637520
DTXSID
DTXSID5044314
ChEMBL
CHEMBL55060
ChEBI
CHEBI:6857
UNII
533CV2ZCQL
EC Number
203-093-8、642-005-6
Nikkaji
J2.848G、J43.384E

Properties

Computed structural properties

XLogP
2.6
Topological polar surface area
26.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
3
Heavy atoms
12

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Esters, Other
SpringerMaterials PropertiesChemical shift
Fragrances · 2 items

Fragrance Ingredient (Methyl cinnamate) -> IFRA transparency List

Fragrance

Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility · 2 items

insoluble in water; soluble in oils

moderately soluble (in ethanol)

Physicochemical properties

Melting point
34 · 34-38 °C(lit.)
Boiling point
260 · 260-262 °C(lit.)
Density
1.078 · 1.078
refractive index
1.5766 · 1.5766
FEMA
2698 · 2698 | METHYL CINNAMATE
Flash point
230 °F · >230 °F

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 17.1% (298 of 1745) of reports.

Warning

H317 (82.9%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1745 reports by companies from 6 notifications to the ECHA C&L Inventory.

Warning

Hazard information

Regulatory Information · 5 items

Chemical: 2-Propenoic acid, 3-phenyl-, methyl ester

Regulation (EC) No 1831/2003 (amended)

2-Propenoic acid, 3-phenyl-, methyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, 3-phenyl-, methyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 07-03-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/12366

2-Propenoic acid, 3-phenyl-, methyl ester: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 2-Propenoic acid, 3-phenyl-, methyl ester: Human health tier I assessment
Hazards SummarySafe when used as a flavoring agent in food; [JECFA] May cause irritation; [Sigma-Aldrich MSDS]
Hazard Classes and Categories · 2 items

Skin Sens. 1 (82.9%)

Skin Sens. 1B (91.7%)

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
1
rtecs
GE0190000
hs_code
2916399090
Signal word
Warning
Symbol(GHS)
GHS07

Chemistry & industry

Uses & manufacturing

UsesPermitted for use as an inert ingredient in non-food pesticide products; [EPA] Used as a fragrance and flavoring agent; [Merck Index]
U.S. Production2023: 175 lb
Consumer UsesFragrance
Household ProductsInformation on 32 consumer products that contain Methyl Cinnamate in the following categories is provided:
Use Classification · 3 items

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

General Manufacturing Information2-Propenoic acid, 3-phenyl-, methyl ester: ACTIVE

Applications

UsesMethyl trans-cinnamate was used to inhibit monophenolase and diphenolase activity of mushroom tyrosinase.

General DescriptionMethyl trans-cinnamate has antimicrobial ability.

Suppliers57 total

盐城通铭生物科技有限公司15195160625 · [email protected]
艾吉析科技（上海）有限公司17717235263 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
上海腾准生物科技有限公司19821570922 · [email protected]
Suzhou ARTK Medchem Co., Ltd.+86-18168183658 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Methyl cinnamate is a methyl ester resulting from the formal condensation of methyl cinnamic acid with methanol. It is found naturally in the essential oils of Alpinia and Basil leaf oil, and widely used in the flavor and perfume industries. It has a role as a flavouring agent, a fragrance, an insect attractant, a volatile oil component and an anti-inflammatory agent. It is a methyl ester and an alkyl cinnamate.

Related reactions

24 records
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Compound notes

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