o-Vanillin

HCID 8991CAS 148-53-8
Substructure searchFind similar structures

Basic information

Standard SMILES
COc1cccc(C=O)c1O
InChIKey
JJVNINGBHGBWJH-UHFFFAOYSA-N
Molecular formula
C8H8O3
Average molar mass
152.15 g/mol
Monoisotopic mass
152.04734412

Overview

Ortho-vanillin is a member of the class of benzaldehydes that is salicylaldehyde substituted by a methoxy group at position 3. It has a role as an antimutagen and a plant metabolite. It is a member of guaiacols and a member of benzaldehydes. It is functionally related to a salicylaldehyde.

Names & identifiers

Preferred name
o-Vanillin
IUPAC
2-hydroxy-3-methoxybenzaldehyde
English name
3-Methoxysalicylaldehyde
Molecular formula
C8H8O3
Molecular weight
152.15

Names & synonyms

2-Hydroxy-3-methoxybenzaldehyde148-53-8O-VANILLIN2-Vanillin6-FormylguaiacolOrthovanillineBenzaldehyde, 2-hydroxy-3-methoxy-6-Formyl-2-methoxyphenol3-Methoxy-2-hydroxybenzaldehydem-Anisaldehyde, 2-hydroxy-Oxy-2 methoxy-3 benzaldehyde008LR748FI
Show more names
Ortho vanillinO-VANILLIN (2-HYDROXY-3-METHOXYBENZALDEHYDE)NC 005NSC 2150
NSC-2150DTXSID5022011o-vanilinRefChem:87386DTXCID902011205-715-33-Methoxysalicylaldehydeortho-vanillin

Database identifiers

CAS
148-53-8
PubChem CID
8991
DTXSID
DTXSID5022011
ChEMBL
CHEMBL13859
ChEBI
CHEBI:78339
UNII
008LR748FI
EC Number
205-715-3
Nikkaji
J45.622E

Properties

Computed structural properties

XLogP
1.4
Topological polar surface area
46.5 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
2
Heavy atoms
11

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Plant Oils and Extracts
SpringerMaterials PropertiesBoiling point
Vapor Pressure0.00103 [mmHg]
Physical DescriptionLight yellow crystalline solid; [Sigma-Aldrich MSDS]

Physicochemical properties

Melting point
40 · 40-42 °C (lit.)
Boiling point
265 · 265-266 °C (lit.)
Density
1.2143 · 1.2143 (rough estimate)
refractive index
1.4945 · 1.4945 (estimate)
Flash point
230 °F · >230 °F
storage temp.
30 °C · Store below +30°C.

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 4.5% (3 of 66) of reports.

Danger

H302 (65.2%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P272, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 66 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Chemical: Benzaldehyde, 2-hydroxy-3-methoxy-

Benzaldehyde, 2-hydroxy-3-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 SummaryA mild eye irritant; Causes convulsions in intraperitoneal lethal-dose studies of guinea pigs and mice; [RTECS] A skin and strong eye irritant; Harmful by ingestion; [Sigma-Aldrich MSDS] See Vanillin.
Hazard Classes and CategoriesAcute Tox. 4 (65.2%)

Safety data

F
10-23
PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
CU6530000
hs_code
29124900

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationBenzaldehyde, 2-hydroxy-3-methoxy-: ACTIVE
Applications · 3 items

Useso-Vanillin has been used to study the solvent-free reaction between o-vanillin and p-toluidine using NMR, DSC and XRD analysis. It was used in the synthesis of new ligand for Fe(III) and Al(lII). It is also used in the study of mutagenesis and as a synthetic precursor for pharmaceuticals.

Useso-Vanillin has been used to study the solvent-free reaction between o-vanillin and p-toluidine using NMR, DSC and XRD analysis. It was used in the synthesis of new ligand for Fe(III) and Al(lII).

UsesA positional isomer of Vanillin. o-Vanillin is a more potent antioxidant than Vanillin.

Upstream & downstream products

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
韶远科技（上海）有限公司021-50795510 4000665055 · [email protected]

Additional notes

DefinitionChEBI: A member of the class of benzaldehydes that is salicylaldehyde substituted by a methoxy group at position 3.

Related reactions

110 records
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Linked notes

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