4-hydroxy-3-methoxybenzaldehyde

• ChemBase ID: 68539
• Molecular Formular: C8H8O3
• Molecular Mass: 152.14732
• Monoisotopic Mass: 152.04734412
• SMILES: C(=O)c1cc(c(cc1)O)OC
• Canonical SMILES: COc1cc(C=O)ccc1O
• InChI: InChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3
• InChIKey: MWOOGOJBHIARFG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxy-3-methoxybenzaldehyde
• IUPAC Traditional name: vanillin
• Synonyms: 4-Hydroxy-3-methoxybenzaldehyde; Vanillinum; 4-Hydroxy-3-(methoxy)benzaldehyde; 2-(Methoxy)-4-formylphenol; p-Vanillin; 3-(Methoxy)-4-hydroxybenzaldehyde; 4-Formyl-2-(methoxy)phenol; 4-Hydroxy-m-anisaldehyde; H 0264; Lioxin; Rhovanil; Vanillaldehyde; NSC 403658; NSC 15351; 4-Hydroxy-3-methoxy-benzaldehyde; VANILLIN; Methyl vanillin; Vanilin; Vanillic aldehyde; Vanillin; 4-Hydroxy-3-methoxybenzaldehyde; Vanillin; Mettler-Toledo® Calibration substance ME 51143093, Vanillin; 香兰素; 4-羟基-3-甲氧苯甲醛; 香草醛; 香草醛; Mettler-Toledo® 校准物质 ME 51143093，香草醛

Database IDs

• CAS Number: 121-33-5
• EC Number: 204-465-2
• MDL Number: MFCD00006942
• Beilstein Number: 472792
• Merck Index: 149932
• PubChem SID: 162034270; 24901469; 24890052; 24901470; 24900708; 24900731; 24890051
• PubChem CID: 1183
• CHEBI ID: 18346
• CHEMBL: 13883
• Chemspider ID: 13860434
• FEMA ID: 3107
• Gmelin ID: 3596
• KEGG ID: D00091
• MeSH Name: vanillin
• Unique Ingredient Identifier: CHI530446X
• Wikipedia Title: Vanillin
• Council of Europe Number: 107
• Flavis Number: 5.018

CALCULATED PROPERTIES

• Acid pKa: 7.807246
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.222392
• LogD (pH = 7.4): 1.0822749
• Log P: 1.2245116
• Molar Refractivity: 41.0861 cm^3
• Polarizability: 15.3633 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 10 g dm^-3 in water; Chloroform; Ethyl Acetate; methanol: soluble0.1 g/mL, clear
• Apperance: White crystals; White Solid
• Melting Point: 80.85 - 82.85°C (354 - 356 K); 80-81°C; 81-83 °C; 81-83 °C(lit.); 81-83°C; 82-84°C
• Boiling Point: 170 °C/15 mmHg(lit.); 170°C/15mm; 285°C
• Flash Point: 147 °C; 153 °C; 153°C(307°F); 307.4 °F
• Density: 1.056 g cm^-3; 1.056 g/ml; 1.06
• Vapor Pressure: >0.01 mmHg ( 25 °C); >1 Pa; 2.2 x 10-3 mm Hg at 25 °C
• Vapor Density: 5.3 (vs air)
• Partition Coefficient: 1.208
• pKa: 7.781
• pKb: 6.216
• Odor: Vanilla, Sweet, Balsamic, Pleasant
• Std enthalpy of combustion: -3.828--3.828 MJ mol^-1
• Organoleptic: caramel; chocolate; sweet; vanilla

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C), Desiccate, Protect from light
• Storage Warning: Air & Light Sensitive; IRRITANT
• RTECS: YW5775000
• European Hazard Symbols: X; Irritant (Xi); Harmful (Xn)
• German water hazard class: 1
• Risk Statements: 20/22; 22-36-43-62-68; 36; R:22-36/37/38; R22
• Safety Statements: 26; 26-36/37; 9-36-60; S:25-26-36/37/39
• TSCA Listed: false; 是
• GHS Pictograms: GHS exclamation mark; GHS07; GHS08
• GHS Signal Word: WARNING; Warning
• NFPA704:
  

  1

  1

  0
• GHS Hazard statements: 302, 317, 319; H302-H317-H319-H341-H361; H302-H332; H319
• GHS Precautionary statements: 280, 305+351+338; P261-P264-P304+P340-P301+P312-P312-P501A; P280-P305 + P351 + P338; P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Regulation Compliance: EU Regulation 1334/2008 & 178/2002; FCC; FDA 21 CFR (182.60); FDA 21 CFR (182.90)

Pharmacology Properties

• Target: Others
• Gene Information: rat ... Ar(24208)
• Allergens: no known allergens; soybeans

Product Information

• Purity: ≥97%; ≥98%; ≥98.0%; ≥98.0% (HPLC); 95+%; 97%; 99%
• Grade: FG; Halal; JIS special grade; Kosher; natural; NI; Ph Eur; purum; ReagentPlus®
• Salt Data: Free Base
• Impurities: <0.500 ppm Soy
• Shelf Life: (limited shelf life, expiry date on the label)
• Quality: traceable to primary standards (LGC)
• Pharmacopeia: testing & handling conforms to Pharmacopeia
• Pharmacopeia Traceability: traceable to USP 1711009
• Linear Formula: 4-(HO)C6H3-3-(OCH3)CHO

DETAILS

MP Biomedicals - 02152188

Crystalline
Purity: 99%

Sigma Aldrich - W310700

Packaging
1 kg in poly bottle
10 kg in poly drum
1 sample in glass bottle
25 kg in fiber drum

Sigma Aldrich - W310727

Other Notes
produced from rice bran ferulic acid

Sigma Aldrich - 77634

Application
For the calibration of METTLER TOLEDO® melting point instruments.
Legal Information
Mettler-Toledo is a registered trademark of Mettler-Toledo, Inc.

Sigma Aldrich - V1104

Packaging
100, 500 g in poly bottle
2 kg in poly drum
2 g in glass bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. V1104.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - V097500

The primary component of Vanilla bean extract.

REFERENCES

• Nazeruddin, G., et al.: Res. J. Pharm., Biol. Chem. Sci., 2, 71 (2011)
• Yang, X., et al.: Biores. Technol., 102, 3498 (2011)