Basic information
- Standard SMILES
COC(=O)c1ccc(OC)cc1- InChIKey
DDIZAANNODHTRB-UHFFFAOYSA-N- Molecular formula
- C9H10O3
- Average molar mass
- 166.17 g/mol
- Monoisotopic mass
- 166.06299418
Overview
Methyl p-anisate is a benzoate ester obtained by the formal condensation of the carboxy group of 4-methoxybenzoic acid with methanol. It is a monomethoxybenzene and a benzoate ester. It is functionally related to a 4-methoxybenzoic acid.
Names & identifiers
- Preferred name
- Methyl anisate
- IUPAC
- methyl 4-methoxybenzoate
- English name
- Methyl anisate
- Molecular formula
- C9H10O3
- Molecular weight
- 166.17
Names & synonyms
METHYL 4-METHOXYBENZOATE121-98-2Methyl anisateMethyl p-anisateBenzoic acid, 4-methoxy-, methyl esterMethyl p-methoxybenzoate4-Methoxybenzoic acid methyl esterMethyl 4-Anisatep-Anisic acid, methyl esterp-Methoxybenzoic acid methyl esteranisateFEMA No. 2679
Show more names
FEMA 2679Methyl anisate, 10 mM in DMSOMethyl-p-anisatMethyl anisate,99%PARA-METHYLANISATE
Benzoic acid, p-methoxy-, methyl esterNSC 7324NSC-73244-methoxy methylbenzoateDTXSID7047645EINECS 204-513-2BRN 2208571CHEBI:86903
Database identifiers
- CAS
121-98-2- PubChem CID
- 8499
- DTXSID
DTXSID7047645- ChEMBL
CHEMBL1762668- ChEBI
CHEBI:86903- UNII
- 2MFL7873W9
- EC Number
- 204-513-2
- Nikkaji
- J33.855I
Properties
Computed structural properties
- XLogP
- 2.3
- Topological polar surface area
- 35.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 148
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Esters, Other
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
FragrancesFragrance Ingredient (Methyl anisate) -> IFRA transparency List
LogP
2.27
2.27
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility
0.643 mg/mL at 20 °C
very slightly soluble in water; soluble in organic solvents, oils
soluble (in ethanol)
Boiling Point
244.00 to 245.00 °C. @ 760.00 mm Hg
255 °C
Melting Point48 °C
Physical Description
White crystalline solid; [Sigma-Aldrich MSDS]
Solid
white crystals with a sweet, floral odour
Physicochemical properties
- Melting point
- 47 · 47-51 °C (lit.)
- Boiling point
- 244 · 244-245 °C (lit.)
- Density
- 1.1708 · 1.1708 (rough estimate)
- refractive index
- 1.5224 · 1.5224 (estimate)
- FEMA
- 2679 · 2679 | METHYL ANISATE
- FLAVIS Number
- 9.713 · 09.713 | Methyl 4-methoxybenzoate
- Flash point
- 230 °F · >230 °F
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Chloroform, Methanol (Slightly)
- form
- Solid
- color
- 2 O · Plates from alcohol. Flakes from EtOH or Et2O
- Odor
- 100 % · at 100.00 %. herbal anise sweet
- Odor Type
- anisic
- biological source
- synthetic
- Water Solubility
- 643.1 mg/L · 643.1mg/L(20 ºC)
- JECFA Number
- 884 · 884
- BRN
- 2208571 · 2208571
- Dielectric constant
- 4.3 · 4.3(33℃)
- Major Application
- flavors and fragrances
- Cosmetics Ingredients Functions
- PERFUMING
- InChI
- 1S/C9H10O3/c1-11-8-5-3-7(4-6-8)9(10)12-2/h3-6H,1-2H3
- InChIKey
- DDIZAANNODHTRB-UHFFFAOYSA-N
- SMILES
- COC(=O)c1ccc(OC)cc1
- LogP
- 2.27 · 2.27
- CAS DataBase Reference
- 121 · 121-98-2(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- METHYL ANISATE
- FDA 21 CFR
- 172.515 · 172.515
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 2 MFL7873W9 · 2MFL7873W9
- NIST Chemistry Reference
- 4 · Benzoic acid, 4-methoxy-, methyl ester(121-98-2)
- EPA Substance Registry System
- 4 · Benzoic acid, 4-methoxy-, methyl ester (121-98-2)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P301+P312-P302+P352-P304+P340-P305+P351+P338
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 22 · 22-24/25
- WGK Germany
- 2 · 2
- RTECS
- 4925000 · BZ4925000
- TSCA
- TSCA listed
- HS Code
- 29189900 · 29189900
- Storage Class
- 11 · 11 - Combustible Solids
- Toxicity
- 50 orl-rat: · LD50 orl-rat: >5 g/kg FCTXAV 14,481,76
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 100% (170 of 170) of all reports.
Not Classified
Aggregated GHS information provided per 170 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: Benzoic acid, 4-methoxy-, methyl ester
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Benzoic acid, 4-methoxy-, methyl ester: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
A mild skin irritant; [RTECS] Fragrance ingredient with positive human patch test results (1 of 182 patients), but insufficient data to classify as established contact allergen in humans; [EC: SCCS] Safe when used as a flavoring agent in food; [JECFA] A mild skin irritant; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesNot Classified
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- BZ4925000
- hs_code
- 29189900
- Toxicity
- LD50 orl-rat: >5 g/kg FCTXAV 14,481,76
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P301+P312-P302+P352-P304+P340-P305+P351+P338
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Uses & manufacturing
UsesUsed as a flavoring agent; [FDA]
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing InformationBenzoic acid, 4-methoxy-, methyl ester: ACTIVE
Applications
DescriptionMethyl anisate is the methyl ester of p-anisic acid.
OccurrenceReported found in the mushroom variety Trametes graveolens, feyoa fruit and peel (Feijoa sellowiana), white wine, cocoa, tea, guava, starfruit, Bourbon vanilla, Tahiti vanilla, mountain papaya, sapodilla fruit and Illicium verum.
UsesMethyl p-anisate has been used as a standard for the quantification of odorant compounds in French mimosa absolute oil by GC-Sniffing.
General DescriptionMethyl p-anisate is a volatile compound released from Mycobacterium tuberculosis and is detected in the breath of tuberculosis patients. It is a potential biomarker for mycobacteria.
Preparation methods
PreparationBy esterification of anisic acid with methanol or from sodium anisate, dimethyl sulfate and small amounts of methanol.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: A benzoate ester obtained by the formal condensation of the carboy group of 4-methoxybenzoic acid with methanol.
Related reactions
30 records
Linked notes
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