4-(4-hydroxy-3-methoxyphenyl)butan-2-one

• ChemBase ID: 72995
• Molecular Formular: C11H14O3
• Molecular Mass: 194.22706
• Monoisotopic Mass: 194.09429431
• SMILES: c1c(c(cc(c1)CCC(=O)C)OC)O
• Canonical SMILES: COc1cc(CCC(=O)C)ccc1O
• InChI: InChI=1S/C11H14O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h5-7,13H,3-4H2,1-2H3
• InChIKey: OJYLAHXKWMRDGS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(4-hydroxy-3-methoxyphenyl)butan-2-one
• IUPAC Traditional name: zingerone
• Synonyms: Vanillylacetone; Zingerone; Vanillylacetone; ZINGERONE; Vanillylacetone; 4-(4-Hydroxy-3-methoxyphenyl)-2-butanone; 4-(4-hydroxy-3-methoxyphenyl)butan-2-one; 姜油酮; 姜酮; 4-(4-羟基-3-甲氧基苯)-2-丁酮

Database IDs

• CAS Number: 122-48-5
• EC Number: 204-548-3
• MDL Number: MFCD00048232
• PubChem SID: 162037915; 24901474
• PubChem CID: 31211
• CHEBI ID: 68657
• CHEMBL: 25894
• Chemspider ID: 28952
• FEMA ID: 3124
• Unique Ingredient Identifier: 4MMW850892
• Wikipedia Title: Zingerone
• Council of Europe Number: 139
• Flavis Number: 7.005

CALCULATED PROPERTIES

• Acid pKa: 9.945876
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.9239362
• LogD (pH = 7.4): 1.9227259
• Log P: 1.9239517
• Molar Refractivity: 53.9618 cm^3
• Polarizability: 20.889801 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 39-42; 40°C; 40-41 °C(lit.); 40–41 °C
• Boiling Point: 141 °C/0.5 mmHg(lit.); 187°C; 187–188 °C at 14 mmHg
• Flash Point: 113 °C; 235.4 °F
• Density: 1.14 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.541(lit.)
• Organoleptic: clove; creamy; spicy; sweet; animal

Safety Information

• Storage Condition: -20°C
• RTECS: EL8900000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335-H303
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C
• Regulation Compliance: FDA 21 CFR (184.1099)

Pharmacology Properties

• Allergens: no known allergens

Product Information

• Purity: ≥96%; 97%
• Grade: Halal; NI
• Salt Data: Free Base
• Linear Formula: 4-(HO)C6H3-3-(OCH3)CH2CH2COCH3
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 05219828

MP Biomedicals Rare Chemical collection

Selleck Chemicals - S2371

Research Area: Endocrinology
Biological Activity:
Vanillylacetone is similar in chemical structure to other flavor chemicals such as vanillin and eugenol. It is used as a flavor additive in spice oils and in perfumery to introduce spicy aromas.Fresh ginger does not contain vanillylacetone; cooking the ginger transforms gingerol, which is present, into vanillylacetone through a retro-aldol reaction. Vanillylacetone is likely the active constituent responsible for the antidiarrheal efficacy of ginger. [1]

Sigma Aldrich - W312401

Biochem/physiol Actions
Taste at 20 ppm in 5%
Other Notes
Natural occurrence: Cranberry and ginger.
Packaging
1 kg in poly bottle
1 sample in glass bottle
100, 250 g in poly bottle

REFERENCES

• http://en.wikipedia.org/wiki/Vanillylacetone