Methyl Vanillate

HCID 19844
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Substructure searchFind similar structures

Basic information

CAS
3943-74-6
Standard SMILES
COC(=O)c1ccc(O)c(OC)c1
InChIKey
BVWTXUYLKBHMOX-UHFFFAOYSA-N
Molecular formula
C9H10O4
Average molar mass
182.17 g/mol
Monoisotopic mass
182.0579088

Overview

Methyl vanillate is a benzoate ester that is the methyl ester of vanillic acid. It has a role as an antioxidant and a plant metabolite. It is a member of phenols, an aromatic ether and a benzoate ester. It is functionally related to a vanillic acid.

Names & identifiers

Preferred name
Methyl Vanillate
IUPAC
methyl 4-hydroxy-3-methoxybenzoate
English name
Methyl vanillate
Molecular formula
C9H10O4
Molecular weight
182.17

Names & synonyms

Methyl vanillate3943-74-6Methyl 4-hydroxy-3-methoxybenzoateMethyl 3-methoxy-4-hydroxybenzoateVanillic acid, methyl ester4-Hydroxy-3-methoxybenzoic acid methyl esterBENZOIC ACID, 4-HYDROXY-3-METHOXY-, METHYL ESTER2HXG8QSO3D4-hydroxy-3-methoxy methyl benzoateNSC-74385DTXSID5074345CHEBI:46477
Show more names
62-65oCMethylevanillateMethylVanillate>TIMTEC-BB SBB008281RARECHEM AL BF 0101Eugenol Impurity 26Methyl vanillate 99%
RefChem:158055DTXCID6039631223-525-9Vanillic acid methyl esterVanillic acid methylMFCD00008438methyl 4-hydroxy-3-methoxy-benzoateAKOS000120673

Database identifiers

CAS
3943-74-6
PubChem CID
19844
DTXSID
DTXSID5074345
ChEMBL
CHEMBL486214
ChEBI
CHEBI:46477
UNII
2HXG8QSO3D
EC Number
223-525-9
Nikkaji
J45.025A

Properties

Computed structural properties

XLogP
1.8
Topological polar surface area
55.8 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
3
Heavy atoms
13

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
FragrancesFragrance Ingredient (Methyl vanillate) -> IFRA transparency List
Flavoring AgentsEU Flavoring substances
Endocrine DisruptorsPotential endocrine disrupting compound

Physicochemical properties

Melting point
64 · 64-67 °C (lit.)
Boiling point
285 · 285-287 °C (lit.)
Density
1.2481 · 1.2481 (rough estimate)
refractive index
1.45 · 1.4500 (estimate)
FLAVIS Number
9.799 · 09.799 | Methyl vanillate
Flash point
285 · 285-287°C

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 82.7% (235 of 284) of all reports.

Warning

H315 (16.9%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 284 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 4 items

Chemical: Benzoic acid, 4-hydroxy-3-methoxy-, methyl ester

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.

Benzoic acid, 4-hydroxy-3-methoxy-, methyl ester: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Benzoic acid, 4-hydroxy-3-methoxy-, methyl ester: Environment tier I assessment
Hazard Classes and CategoriesSkin Irrit. 2 (16.9%)

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
DH2430000
hs_code
29189900
risk_code
36/37/38

Chemistry & industry

Uses & manufacturing

Use ClassificationFragrance Ingredients
General Manufacturing InformationBenzoic acid, 4-hydroxy-3-methoxy-, methyl ester: ACTIVE
Applications · 3 items

UsesMethyl vanillate is used to investigate the volatile compounds of heather honeys from Calluna vulgaris and Erica arborea.

UsesMethyl Vanillate maintains antimicrobial properties due to the phenylpropanoid moiety in the structure.

General DescriptionMethyl vanillate is a volatile compound present in cloudberries (Rubus Chamaemorus.). Methyl vanillate can be synthesized from vanillic acid. Methyl vanillate has been identified in foods such as cow's milk and beer.

Upstream & downstream products

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
杭州创引化工科技有限公司0571-87086220 13516718938 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
宁夏信达昌科技有限公司13832371507
Additional notes · 1 item

DefinitionChEBI: Methyl vanillate is a benzoate ester that is the methyl ester of vanillic acid. It has a role as an antioxidant and a plant metabolite. It is a benzoate ester, a member of phenols and an aromatic ether. It is functionally related to a vanillic acid.

Related reactions

121 records
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Compound notes

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