Basic information
- CAS
579-75-9- Standard SMILES
COc1ccccc1C(=O)O- InChIKey
ILUJQPXNXACGAN-UHFFFAOYSA-N- Molecular formula
- C8H8O3
- Average molar mass
- 152.15 g/mol
- Monoisotopic mass
- 152.04734412
Overview
O-methylsalicylic acid is a methoxybenzoic acid that is the methyl ether of salicylic acid. It has a role as a non-steroidal anti-inflammatory drug and a flavouring agent. It is a conjugate acid of an O-methylsalicylate.
Names & identifiers
- Preferred name
- 2-Methoxybenzoic acid
- IUPAC
- 2-methoxybenzoic acid
- English name
- o-Anisic acid
- Molecular formula
- C8H8O3
- Molecular weight
- 152.15
Names & synonyms
2-METHOXYBENZOIC ACIDo-Anisic acid579-75-9O-Methylsalicylic acido-Methoxybenzoic acidBenzoic acid, 2-methoxy-2-Anisic acidSalicylic acid methyl ether49WA6Z7GZACHEBI:421840NSC-3778DTXSID3060376
Show more names
2-methoxybenzoic2-methoxy-benzoicacio-anisicNSC 3778FEMA 3943o-Anissureo-Anisc Acid
FEMA NO. 3943RefChem:87897DTXCID6042282209-447-8529-75-92-Methoxy-benzoic acidMFCD00002431O-Methoxy benzoic acid
Database identifiers
- CAS
579-75-9- PubChem CID
- 11370
- DTXSID
DTXSID3060376- ChEMBL
CHEMBL192311- ChEBI
CHEBI:421840- UNII
- 49WA6Z7GZA
- EC Number
- 209-447-8
- Nikkaji
- J7.431D
Properties
Computed structural properties
- XLogP
- 1.6
- Topological polar surface area
- 46.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 144
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Benzoic Acid Derivatives
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP
1.59
1.62
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Solubility
5 mg/mL at 30 °C
soluble in boiling water, organic solvents
freely soluble (in ethanol)
Boiling Point
279.00 to 280.00 °C. @ 760.00 mm Hg
200 °C
Melting Point106 °C
Physical Description
White odorless powder; [Alfa Aesar MSDS]
Solid
white crystalline needles with practically no odour
Physicochemical properties
- Melting point
- 98 · 98-100 °C(lit.)
- Boiling point
- 200 °C · 200°C
- Density
- 1.2143 · 1.2143 (rough estimate)
- vapor pressure
- 0.002 Pa · 0.002Pa at 25℃
- refractive index
- 1.4945 · 1.4945 (estimate)
- FEMA
- 3943 · 3943 | 2-METHOXYBENZOIC ACID
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- 5 g/l · 5g/l
- form
- Crystalline Powder
- pka
- 4.09 · 4.09±0.10(Predicted)
- color
- White to off-white
- Odor
- odorless
- Water Solubility
- 4.2 g/L · 4.2g/L(25 ºC)
- JECFA Number
- 881 · 881
- BRN
- 509929 · 509929
- Henry's Law Constant
- 2.5 · 2.5×103 mol/(m3Pa) at 25℃, Abraham and Jr. (2019)
- InChI
- 1S/C8H8O3/c1-11-7-5-3-2-4-6(7)8(9)10/h2-5H,1H3,(H,9,10)
- InChIKey
- ILUJQPXNXACGAN-UHFFFAOYSA-N
- SMILES
- COc1ccccc1C(O)=O
- LogP
- 2.046 at · 2.046 at 25℃
- CAS DataBase Reference
- 579 · 579-75-9(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- 2 · 2-METHOXYBENZOIC ACID
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 49 WA6Z7GZA · 49WA6Z7GZA
- NIST Chemistry Reference
- 2 · Benzoic acid, 2-methoxy-(579-75-9)
- EPA Substance Registry System
- 2 · Benzoic acid, 2-methoxy- (579-75-9)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319
- Precautionary statements
- 264 · P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Hazard Codes
- Xi
- Safety Statements
- 24 · 24/25
- WGK Germany
- 3 · 3
- RTECS
- 4385000 · BZ4385000
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HS Code
- 29189090 · 29189090
- Storage Class
- 11 · 11 - Combustible Solids
- REACH Registrations
- Inactive
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 1.6% (2 of 127) of reports.
Warning
H315 (98.4%): Causes skin irritation [Warning Skin corrosion/irritation]
P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)
Aggregated GHS information provided per 127 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Benzoic acid, 2-methoxy-
Status: No longer Valid Update: 04-05-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/19224
Benzoic acid, 2-methoxy-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazards Summary
Causes excitement and muscle contraction or spasticity in intravenous and intraperitoneal lethal-dose studies of rats (intravenous LDLo = 2,750 mg/kg); [RTECS] Safe when used as a flavoring agent in food; [JECFA] May cause irritation; [Alfa Aesar MSDS] See Benzoic acid. See Anisole.
Hazard Classes and CategoriesSkin Irrit. 2 (98.4%)
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- BZ4385000
- hs_code
- 29189090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- hazard_note
- Irritant
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319
- REACH Registrations
- Inactive
- Precautionary statements
- P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Uses & manufacturing
UsesUsed as a flavoring agent; [FDA]
Use Classification
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
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing InformationBenzoic acid, 2-methoxy-: ACTIVE
Applications
Uses2-Methoxybenzoic Acid is used in the preparation of benzohydroxamic acids as potent and selective anti-hepatitis C virus (HCV) agents.
Uses2-Methoxybenzoic acid was used as internal standard during quantification of free and conjugated salicylic acid in tomato (Lycopersicon esculentum) cells by HPLC. It was also employed in the synthesis of pthalides.
General Description2-Methoxybenzoic acid was added as carbon supplement in the culture medium of Moraxella osloensis. Photophysics of 2-methoxybenzoic acid has been investigated using both the time-correlated single photon counting and the fluorescence up-conversion techniques.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: A methoxybenzoic acid that is the methyl ether of salicylic acid.
Related reactions
107 records
Compound notes
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