Vanillin
Athanor · official
C8H8O3 · 152.15 g/mol
IUPAC name: 4-hydroxy-3-methoxybenzaldehyde
Also called vanilla, 4-hydroxy-3-methoxybenzaldehyde, vanillic aldehyde
WarningMay cause an allergic skin reaction · Causes serious eye irritationNames and identifiers
- IUPAC name
- 4-hydroxy-3-methoxybenzaldehyde
- Synonyms
- vanilla, 4-hydroxy-3-methoxybenzaldehyde, vanillic aldehyde
+ 38 more
4-Hydroxy-3-methoxybenzaldehyde, Vanillic aldehyde, Vanillaldehyde, p-Vanillin, Vanilline, Lioxin, 3-Methoxy-4-hydroxybenzaldehyde, 4-Hydroxy-3-methoxy-benzaldehyde, Benzaldehyde, 4-hydroxy-3-methoxy-, 4-Hydroxy-m-anisaldehyde, 2-Methoxy-4-formylphenol, Zimco, p-Hydroxy-m-methoxybenzaldehyde, 4-Formyl-2-methoxyphenol, Methylprotocatechuic aldehyde, 4-Hydroxy-5-methoxybenzaldehyde, m-Anisaldehyde, 4-hydroxy-, Protocatechualdehyde, methyl-, Rhovanil, FEMA No. 3107, vaniline, Protocatechualdehyde 3-methyl ether, Oleoresin vanilla, m-Methoxy-p-hydroxybenzaldehyde, Vanillin Melting Point Standard, DTXSID0021969, NSC-15351, NSC-48383, NSC-403658, 4-hydroxy-3-methoxy-benzyldehyde, NPLC-0145, CHI530446X, DTXCID301969, CHEBI:18346, H-0264, NSC15351, Vanillin,, RefChem:6510
- Molecular formula
- C8H8O3
- Empirical formula
- C8H8O3
- Molecular weight
- 152.15 g/mol
- Exact mass
- 152.04734
- CAS number
- 121-33-5
- PubChem CID
- 1183
- Canonical SMILES
- COC1=C(C=CC(=C1)C=O)O
- Isomeric SMILES
- COC1=C(C=CC(=C1)C=O)O
- InChI
- InChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3
- InChIKey
- MWOOGOJBHIARFG-UHFFFAOYSA-N
- Molfile
Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.
Physical properties
- Appearance
- White crystalline needles from water[4]
4 values
From Hazardous Substances Data Bank (HSDB), the most authoritative source here.
Value As written Source – Vanillin appears as white or very slightly yellow needles. [1] CAMEO Chemicals – Liquid; Other Solid; Dry Powder; CBI; Large Crystals [2] EPA Chemical Data Reporting (CDR) – WHITE-TO-YELLOW CRYSTALLINE POWDER WITH CHARACTERISTIC ODOUR. [3] ILO-WHO International Chemical Safety Cards (ICSCs) –shown White crystalline needles from water [4] Hazardous Substances Data Bank (HSDB)cites Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 12th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2012., p. 4507 - Odor
- Sweetish smell[4]
- Melting point
- 81 to 83 °C (178 to 181 °F, NTP 1992)[1]
2 values
2 of 2 sources agree on it (most common value).
Value As written Source 81 to 83 °Cshown 178 to 181 °F (NTP, 1992) [1] CAMEO Chemicalscites National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina. 81 to 83 °C 81-83 °C [3] ILO-WHO International Chemical Safety Cards (ICSCs) - Boiling point
- 285 °C[3]
2 values
2 of 2 sources agree on it (most common value).
Value As written Source 285 °C 545 °F at 760 mmHg (NTP, 1992) [1] CAMEO Chemicalscites National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina. 285 °Cshown 285 °C [3] ILO-WHO International Chemical Safety Cards (ICSCs) - Density
- 1.056 at 20 °C (68 °F) (NTP, 1992) - Denser than water[1]
2 values
2 of 2 sources agree on it (most common value).
Value As written Source –shown 1.056 at 68 °F (NTP, 1992) - Denser than water [1] CAMEO Chemicalscites National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina. – 1.06 g/cm³ [3] ILO-WHO International Chemical Safety Cards (ICSCs) - Solubility in water
- Solubility in water, g/100ml at 25 °C: 1.0[3]
4 values
From ILO-WHO International Chemical Safety Cards (ICSCs), the most authoritative source here.
Value As written Source – Slightly soluble (NTP, 1992) [1] CAMEO Chemicalscites National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina. – In water, 1.102X10+4 mg/L at 25 °C [4] Hazardous Substances Data Bank (HSDB)cites Yalkowsky, S.H., He, Yan, Jain, P. Handbook of Aqueous Solubility Data Second Edition. CRC Press, Boca Raton, FL 2010, p. 480 – Soluble in 125 parts water, 20 parts glycerin, 2 parts 95% alcohol, chloroform, ether. [4] Hazardous Substances Data Bank (HSDB)cites Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 12th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2012., p. 4507 –shown Solubility in water, g/100ml at 25 °C: 1.0 [3] ILO-WHO International Chemical Safety Cards (ICSCs) - log P
- 1.21[3]
2 values
Sources disagree; from ILO-WHO International Chemical Safety Cards (ICSCs), the most authoritative.
Value As written Source – log Kow = 1.37 [4] Hazardous Substances Data Bank (HSDB)cites Hansch, C., Leo, A., D. Hoekman. Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society., 1995., p. 42 –shown 1.21 [3] ILO-WHO International Chemical Safety Cards (ICSCs) - pKa
- pKa = 7.4 at 25 °C[4]
- Vapor pressure
- 1 mmHg at 107 °C (225 °F, NTP 1992)[1]
- Flash point
- 153 °C c.c.[3]
2 values
2 of 2 sources agree on it (most common value).
Value As written Source 153 °C 153 °C (307 °F) - closed cup [4] Hazardous Substances Data Bank (HSDB)cites Sigma-Aldrich; Material Safety Data Sheet for Vanillin, Product Number: V2375, Version 5.3 (Revision Date 04/24/2015). Available from, as of December 2, 2015: https://www.sigmaaldrich.com/safety-center.html 153 °Cshown 153 °C c.c. [3] ILO-WHO International Chemical Safety Cards (ICSCs) - Autoignition temperature
- >400 °C[3]
Each value as its source reports it, with the source's number after it (listed under References). Where several sources report a property, the row shows the value most of them agree on, the rule the app uses; open the values to see every one.
Calculated
- Heavy atoms
- 11
- Rings
- 1
- Aromatic rings
- 1
- Fraction sp³ carbons (Fsp3)
- 0.12
- H-bond donors
- 1
- H-bond acceptors
- 3
- Rotatable bonds
- 2
- TPSA (Ų)
- 46.5
- Formal charge
- 0
- XLogP3
- 1.2 PubChem
- Complexity
- 135 PubChem
- Stereocenters
- None
- Double-bond geometry
- None specified
- Point group
- Cs of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)
Elemental analysis
- C63.15%
- H5.30%
- O31.55%
Isotope pattern
Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.
Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.
Predicted
- log P
- 1.21 Crippen (Wildman and Crippen 1999)
- log S (water solubility)
- -1.82 ESOL (Delaney 2004), log mol/L
- Synthetic accessibility
- 1.82 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)
Drug-likeness: Lipinski’s rule of five
- Molecular weight ≤ 500: 152.15
- log P ≤ 5 (Crippen): 1.21
- H-bond donors ≤ 5: 1
- H-bond acceptors ≤ 10: 3
Passes all four rules.
¹³C NMR shifts, predicted
Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.
Safety
Warning
Most widely reported: 2,387 company reports to ECHA. Source [5].
- Harmful or irritant
- H317May cause an allergic skin reaction (14.3% of reports)
- H319Causes serious eye irritation (83.5% of reports)
Precautionary statements: P261, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P333+P317, P337+P317, P362+P364, P501
View all classifications (4)
- [5] European Chemicals Agency (ECHA)This chemical does not meet GHS hazard criteria for 1.8% (42 of 2387) of reports.
- [5] European Chemicals Agency (ECHA) · 2,387 reports · WarningH317, H319
- [5] European Chemicals Agency (ECHA) · WarningH302, H411
- [4] Hazardous Substances Data Bank (HSDB) · WarningH319, H402, H412
First aid
- Eyes: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. Immediately transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. Skin: Immediately flood affected skin with water while removing and isolating all contaminated clothing.[1]
- Fresh air, rest.[3]
- Rinse and then wash skin with water and soap.[3]
- Rinse with plenty of water (remove contact lenses if easily possible).[3]
Storage
Incompatibilities
Safety data sheets on the supplier’s page: Amerigo Scientific, Sigma-Aldrich, Quality Control Solutions (QCS Standards).
Always read the supplier’s safety data sheet before working with it.
Spectra
- NMRHazardous Substances Data Bank (HSDB) · NMRShiftDB
- 1H NMRHuman Metabolome Database (HMDB) (JEOL · 90 MHz · CDCl3) · SpectraBase
- 13C NMRHuman Metabolome Database (HMDB) (Varian · 25.16 MHz · CDCl3) · SpectraBase
- 17O NMRSpectraBase
- GC-MSHuman Metabolome Database (HMDB) (EI-B · positive) · Human Metabolome Database (HMDB) (EI-B · positive) · Human Metabolome Database (HMDB) (EI-B · positive) · Human Metabolome Database (HMDB) (EI-B · positive) · Human Metabolome Database (HMDB) (EI-B · positive) · Human Metabolome Database (HMDB) (GC-EI-TOF · positive)
- MS-MSHuman Metabolome Database (HMDB) (Negative) · Human Metabolome Database (HMDB) (Negative) · Human Metabolome Database (HMDB) (Negative) · Human Metabolome Database (HMDB) (Negative) · Human Metabolome Database (HMDB) (Negative) · Human Metabolome Database (HMDB) (Negative)
- LC-MSMassBank Europe (LTQ Orbitrap Velos Thermo Scientific · LC-ESI-ITFT · NEGATIVE) · MassBank Europe (Thermo_Qexactive_Plus · LC-ESI-QFT · NEGATIVE) · MassBank Europe (Bruker MicrOTOF-Q · LC-ESI-QTOF · POSITIVE) · MassBank Europe (Bruker MicrOTOF-Q · LC-ESI-QTOF · POSITIVE) · MassBank Europe (Bruker MicrOTOF-Q · LC-ESI-QTOF · POSITIVE) · MassBank Europe (Bruker MicrOTOF-Q · LC-ESI-QTOF · NEGATIVE)
- Other MSHazardous Substances Data Bank (HSDB) · MassBank Europe (HITACHI M-80 · EI-B · POSITIVE) · MassBank Europe (HITACHI M-80B · EI-B · POSITIVE) · MassBank Europe (HITACHI M-80A · EI-B · POSITIVE) · MassBank of North America (MoNA) (TQD, Waters · Flow-injection QqQ/MS · ESI) · MassBank of North America (MoNA) (TQD, Waters · Flow-injection QqQ/MS · ESI)
- UVHazardous Substances Data Bank (HSDB)
- UV-VISSpectraBase
- IRHazardous Substances Data Bank (HSDB)
- FTIRSpectraBase (FILM (CAST FROM ACETONE))
- ATR-IRSpectraBase (Bruker Tensor 27 FT-IR · ATR-Neat (DuraSamplIR II))
- Vapor Phase IRSpectraBase (DIGILAB FTS-14 · Vapor Phase)
- RamanSpectraBase (Bruker MultiRAM Stand Alone FT-Raman Spectrometer · FT-Raman)
Experimental spectra held by these sources; each link opens the source's own record.
Literature
Reading PubChem, OpenAlex and GSRS…
Bioactivity
Reading ChEMBL…
References
- [1]CAMEO Chemicals · Public domain (NOAA) · via PubChem · retrieved 2026-10-14
- [2]EPA Chemical Data Reporting (CDR) · Public domain (US EPA) · via PubChem · retrieved 2026-10-14
- [3]ILO-WHO International Chemical Safety Cards (ICSCs) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
- [4]Hazardous Substances Data Bank (HSDB) · Public domain (US NLM) · via PubChem · retrieved 2026-10-14
- [5]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
- [6]NMRShiftDB · Linked only · via PubChem · retrieved 2026-10-14
- [7]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
- [8]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
- [9]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
- [10]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
- [11]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
- ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
- ·Literature on PubChem
Data last updated 2026-10-14.