o-Vanillin
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Basic information
- CAS
148-53-8- 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 propertiesFilling in
- XLogP
- 1.4
- 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
- 135
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.
- solubility
- Chloroform (Sparingly), Methanol (Slightly)
- pka
- 1 · pK1:7.912 (25°C)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
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
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
- risk_code
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationBenzaldehyde, 2-hydroxy-3-methoxy-: ACTIVE
Applications
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
Upstream raw materials
Downstream products
Related reactions
110 records
Compound notes
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