W246000

Sigma-Aldrich

Ethyl tiglate

≥98%, FG

Synonym(s):
Ethyl trans-2-methyl-2-butenoate
Linear Formula:
CH3CH=C(CH3)CO2C2H5
CAS Number:
Molecular Weight:
128.17
FEMA Number:
2460
EC Number:
Council of Europe no.:
2185
MDL number:
PubChem Substance ID:
Flavis number:
9.495
NACRES:
NA.21

Quality Level

biological source

synthetic

grade

FG
Halal
Kosher

Agency/Method

meets purity specifications of JECFA

reg. compliance

EU Regulation 1334/2008 & 178/2002
FDA 21 CFR 117

assay

≥98%

refractive index

n20/D 1.435 (lit.)

bp

154-156 °C (lit.)

density

0.923 g/mL at 25 °C (lit.)

Documentation

see Safety & Documentation for available documents

Featured Industry

Flavors and Fragrances

Organoleptic

berry; caramel; floral; tropical; fruity; sweet

food allergen

no known allergens

SMILES string

CCOC(=O)\C(C)=C\C

InChI

1S/C7H12O2/c1-4-6(3)7(8)9-5-2/h4H,5H2,1-3H3/b6-4+

InChI key

OAPHLAAOJMTMLY-GQCTYLIASA-N

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General description

Ethyl tiglate, an α,β-unsaturated ester, is naturally found in apples. It can be prepared by the esterification of tiglic acid. Ethyl tiglate is a male-specific pheromone found in some Drosophila species that can attract both male and females. Saprochaete suaveolens grown in a culture medium has been reported to produce ethyl tiglate by metabolizing isoleucine.

Packaging

100 g in poly bottle
1 kg in poly bottle
5 kg in poly drum

Other Notes

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Legal Information

For R&D Use and/or Food Manufacturing only

Pictograms

Flame

Signal Word

Warning

Hazard Statements

RIDADR

UN 3272 3 / PGIII

WGK Germany

WGK 2

Flash Point(F)

111.2 °F - closed cup

Flash Point(C)

44 °C - closed cup

Aggregation pheromones in five taxa of the Drosophila virilis species group.
Bartelt RJ, et al.
Physiological Entomology, 11(4), 367-376 (1986)
T Hauck et al.
Enantiomer, 5(5), 505-512 (2001-01-06)
(S)-Ethyl 2-methylbutanoate is an important aroma compound in apples and serves as an indicator for genuineness of apple products due to its high optical purity of greater than 98% enantiomeric excess [T. Koenig and P. Schreier, Zeitsch. Lebensm.-Unters. Forsch. A...
R J Bartelt et al.
Journal of chemical ecology, 14(4), 1319-1327 (1988-04-01)
Mature males ofDrosophila borealis andD. littoralis (Diptera: Drosophilidae) produce pheromones that attract both males and females in a wind-tunnel bioassay. Ethyl tiglate is a major pheromone component in both species. Isopropyl tiglate is a minor component, as active as ethyl...
The preparation of tiglic and angelic acids and esters1.
Buckles RE and Mock GV.
The Journal of Organic Chemistry, 15(3), 680-684 (1950)
Eric Grondin et al.
Yeast (Chichester, England), 32(1), 57-66 (2014-11-20)
A yeast identified as Saprochaete suaveolens was investigated for its capacity to produce a large panel of flavouring molecules. With a production of 32 compounds including 28 esters, S. suaveolens seems to be a good producer of fruity flavours and...

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