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W310700

Sigma-Aldrich

Vanillin

≥97%, FCC, FG

Synonym(s):
4-Hydroxy-3-methoxybenzaldehyde, Vanillic aldehyde
Linear Formula:
4-(HO)C6H3-3-(OCH3)CHO
CAS Number:
Molecular Weight:
152.15
FEMA Number:
3107
Beilstein:
472792
EC Number:
Council of Europe no.:
107
MDL number:
PubChem Substance ID:
Flavis number:
5.018

Quality Level

biological source

synthetic

grade

FG
Halal
Kosher

reg. compliance

EU Regulation 1334/2008 & 178/2002
FCC
FDA 21 CFR 182.60
FDA 21 CFR 182.90

vapor density

5.3 (vs air)

vapor pressure

>0.01 mmHg ( 25 °C)

description

Agency/Method; meets purity specifications of JECFA

assay

≥97%

form

powder or crystals

bp

170 °C/15 mmHg (lit.)

mp

81-83 °C (lit.)

solubility

DMSO: soluble(lit.)

Documentation

see Safety & Documentation for available documents

Organoleptic

creamy; sweet; vanilla

application(s)

flavors and fragrances

food allergen

no known allergens

SMILES string

COc1cc(C=O)ccc1O

InChI

1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3

InChI key

MWOOGOJBHIARFG-UHFFFAOYSA-N

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General description

Vanillin is the world′s most popular flavor and fragrance compound. It may be a potential agent of pharmacological importance and useful for the treatment of major depressive disorder. Eumelanin-inspired core derived from vanillin has been found to be useful for the synthesis of eumelanin-inspired small molecules and polymer via Sonogashira cross coupling. Biotechnology-based vanillin synthesis using ferulic acid, eugenol and glucose as substrates and bacteria, fungi and yeasts as microbial production hosts has been reported. Vanillin, a polar aromatic flavor compound, is present in the extracts of natural and artificial vanilla flavors.

Application

Vanillin is suitable for use in a study to evaluate its sensitizing effect on a tumor necrosis factor-related apoptosis-inducing ligand (TRAIL)-resistant human cervical cancer cell line, HeLa.

Packaging

10 kg in poly drum
1 kg in poly bottle
25 kg in fiber drum

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

319.6 - 321.4 °F - closed cup

Flash Point(C)

159.8 - 160,8 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Nethaji J Gallage et al.
Molecular plant, 8(1), 40-57 (2015-01-13)
In recent years, biotechnology-derived production of flavors and fragrances has expanded rapidly. The world's most popular flavor, vanillin, is no exception. This review outlines the current state of biotechnology-based vanillin synthesis with the use of ferulic acid, eugenol, and glucose
Kriengsak Lirdprapamongkol et al.
In vivo (Athens, Greece), 24(4), 501-506 (2010-07-30)
Tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) is a promising anticancer agent which selectively kills cancer cells with little effect on normal cells. However, TRAIL resistance is widely found in cancer cells. We have previously reported antimetatstatic and antiangiogenic effects of
Subhashini Selvaraju et al.
Chemical communications (Cambridge, England), 51(14), 2957-2959 (2015-01-17)
An eumelanin-inspired core derived from the natural product, vanillin (vanilla bean extract) was utilized for the synthesis of eumelanin-inspired small molecules and polymer via Sonogashira cross coupling. The materials demonstrate that the methyl 4,7-dibromo-5,6-dimethoxy-N-methyl-1H-indole-2-carboxylate core can serve as a new
Determination of vanillin and related flavor compounds in natural vanilla extracts and vanilla-flavored foods by thin layer chromatography and automated multiple development.
Belay MT and Poole CF.
Chromatographia, 37(7-8), 365-373 (1993)
Chia-Lin Lee et al.
Journal of natural products, 72(9), 1568-1572 (2009-08-21)
Two new sesquiterpene coumarins, designated 5'-acetoxy-8'-hydroxyumbelliprenin (1) and 10'R-acetoxy-11'-hydroxyumbelliprenin (2), and a new diterpene, 15-hydroxy-6-en-dehydroabietic acid (3), along with 27 known compounds, were isolated from a CHCl(3)-soluble extract of Ferula assa-foetida through bioassay-guided fractionation. The structures of the new metabolites

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