Basic information
- Standard SMILES
O=C(O)c1cccc(O)c1- InChIKey
IJFXRHURBJZNAO-UHFFFAOYSA-N- Molecular formula
- C7H6O3
- Average molar mass
- 138.12 g/mol
- Monoisotopic mass
- 138.03169405
Overview
3-hydroxybenzoic acid is a monohydroxybenzoic acid that is benzoic acid substituted by a hydroxy group at position 3. It has been isolated from Taxus baccata. It is used as an intermediate in the synthesis of plasticisers, resins, pharmaceuticals, etc. It has a role as a plant metabolite and a bacterial metabolite. It is functionally related to a benzoic acid. It is a conjugate acid of a 3-hydroxybenzoate.
Names & identifiers
- Preferred name
- 3-Hydroxybenzoic Acid
- IUPAC
- 3-hydroxybenzoic acid
- English name
- 3-Hydroxybenzoic acid
- Molecular formula
- C7H6O3
- Molecular weight
- 138.12
Names & synonyms
3-Hydroxybenzoic acid99-06-9M-HYDROXYBENZOIC ACIDm-Salicylic acid3-CarboxyphenolBenzoic acid, 3-hydroxy-Benzoic acid, m-hydroxy-DTXSID60216102ZFW40OJ7UCHEBI:30764NSC-55746AC PE 3HB
Show more names
3-hydroxybenzoatem-salicylicacidm-Salicylic Acim-Hydroxybenzoic
DTXCID6016103-hydroxybenzoic acid, monosodium saltRefChem:25902202-726-5m-Hba3-Hydroxy benzoic acidAcido m-idrossibenzoicometa-Hydroxybenzoic acid
Database identifiers
- CAS
99-06-9- PubChem CID
- 7420
- DTXSID
DTXSID6021610- ChEMBL
CHEMBL65369- ChEBI
CHEBI:30764- UNII
- 2ZFW40OJ7U
- EC Number
- 202-726-5
- Nikkaji
- J43.202D
Properties
Computed structural properties
- XLogP
- 1.5
- Topological polar surface area
- 57.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 133
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Benzoic Acid Derivatives
SpringerMaterials PropertiesChemical bond
LogP1.50
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility
7.25 mg/mL at 25 °C
Soluble
Soluble (in ethanol)
Melting Point202 °C
Vapor Pressure0.000158 [mmHg]
Physical Description
White or off-white powder; [Alfa Aesar MSDS]
Solid
White crystalline powder
Physicochemical properties
- Melting point
- 200 · 200-203 °C (lit.)
- Boiling point
- 213.5 °C · 213.5°C (rough estimate)
- Density
- 1.485 · 1.4850
- refractive index
- 1.46 · 1.4600 (estimate)
- FEMA
- 4431 · 4431 | 3-HYDROXYBENZOIC ACID
- FLAVIS Number
- 8.132 · 08.132 | 3-Hydroxybenzoic acid
- Flash point
- 220 °C · 220 °C
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- DMSO (Slightly), Methanol (Slightly)
- pka
- 4.06 · 4.06(at 19℃)
- form
- Powder
- color
- White to off-white
- PH
- 3 · 3 (H2O)Aqueous solution
- Water Solubility
- slightly soluble
- JECFA Number
- 2279 · 2279
- BRN
- 508160 · 508160
- Cosmetics Ingredients Functions
- SKIN CONDITIONING
- InChI
- 1S/C7H6O3/c8-6-3-1-2-5(4-6)7(9)10/h1-4,8H,(H,9,10)
- InChIKey
- IJFXRHURBJZNAO-UHFFFAOYSA-N
- SMILES
- OC(=O)c1cccc(O)c1
- LogP
- 1.5 · 1.50
- CAS DataBase Reference
- 99 · 99-06-9(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- 3 · 3-HYDROXYBENZOIC ACID
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 2 ZFW40OJ7U · 2ZFW40OJ7U
- NIST Chemistry Reference
- 3 · Benzoic acid, 3-hydroxy-(99-06-9)
- EPA Substance Registry System
- m-Hydroxybenzoic acid (99-06-9)
- 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-P264-P270-P301+P312-P302+P352-P305+P351+P338
- Hazard Codes
- Xn,Xi
- Risk Statements
- 22 · 22-36/37/38
- Safety Statements
- 26 · 26-36-37/39
- WGK Germany
- 3 · 3
- RTECS
- 1924980 · DH1924980
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HS Code
- 29182990 · 29182990
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 OralEye · Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (94%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 50 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Benzoic acid, 3-hydroxy-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
3-Hydroxybenzoic acid: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards SummaryA skin and strong eye irritant; Harmful by ingestion; [Alfa Aesar MSDS] See 4-Hydroxybenzoic acid.
Hazard Classes and CategoriesAcute Tox. 4 (94%)
Safety data
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- DH1924980
- hs_code
- 29182990
- risk_code
- 22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,Xi
- hazard_note
- Irritant
- safety_code
- 26-36-37/39
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Hazard Classifications
- Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P270-P301+P312-P302+P352-P305+P351+P338
Chemistry & industry
Uses & manufacturing
Use Classification
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing InformationBenzoic acid, 3-hydroxy-: ACTIVE
Applications
Uses3-Hydroxybenzoic acid is used as an intermediate in the manufacture of germicides, plasticizers, preservatives, light stabiliziers, petroleum additives, pharmaceuticals, and plasticizer. It can also be used for the synthesis of azo dyes and herbicide fomesafen.
Preparation methods
Preparation3-Hydroxybenzoic acid is synthesized from benzoic acid by sulfonation, alkali melting and hydrolysis. 122kg of benzoic acid was put into the reactor, and 100kg of oleum was added under stirring. The temperature was raised to about 100 °C, and the reaction was carried out for 2h to obtain Sodium 3-sulfobenzoate. Then the sulfonated liquid was transferred to an alkali melting pot, 45 kg of solid sodium hydroxide was added, the temperature was raised to melting, and reacted for 4 to 5 hours to obtain sodium m-carboxyphenate, and diluted sulfuric acid was added for acid hydrolysis. Cool and crystallize, filter out sodium sulfate, and decolorize the filter cake with activated carbon to obtain 3-Hydroxybenzoic acid.
Upstream & downstream products
Upstream raw materials
Downstream products
Additional notes
DefinitionChEBI: 3-hydroxybenzoic acid is a monohydroxybenzoic acid that is benzoic acid substituted by a hydroxy group at position 3. It has been isolated from Taxus baccata. It is used as an intermediate in the synthesis of plasticisers, resins, pharmaceuticals, etc. It has a role as a bacterial metabolite and a plant metabolite. It derives from a benzoic acid. It is a conjugate acid of a 3-hydroxybenzoate.
Related reactions
203 records
Linked notes
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