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Merck
CN

W246000

Ethyl tiglate

≥98%, FG

Synonym(s):

Ethyl trans-2-methyl-2-butenoate

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About This Item

Linear Formula:
CH3CH=C(CH3)CO2C2H5
CAS Number:
5837-78-5
Molecular Weight:
128.17
FEMA Number:
2460
Council of Europe no.:
2185
UNSPSC Code:
12164502
PubChem Substance ID:
329830493
Flavis number:
9.495
EC Number:
227-425-6
NACRES:
NA.21
MDL number:
MFCD00015183
Organoleptic:
berry; caramel; fruity; tropical; floral; sweet
Grade:
FG
Halal
Kosher
Biological source:
synthetic
Agency:
meets purity specifications of JECFA
Food allergen:
no known allergens

Key Documents

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Product Name

Ethyl tiglate, ≥98%, FG

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

biological source

synthetic

grade

FG
Halal
Kosher

agency

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.)

application(s)

flavors and fragrances

documentation

see Safety & Documentation for available documents

food allergen

no known allergens

organoleptic

berry; caramel; fruity; tropical; floral; sweet

Quality Level

300

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Related Categories

Application


  • Metabolism of ethyl tiglate in apple fruits leads to the formation of small amounts of (R)-ethyl 2-methylbutanoate.: Focuses on the metabolic transformation of ethyl tiglate in apples, which contributes to the fruit′s flavor profile (Hauck et al., 2000).

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.

pictograms

Flame
GHS02

signalword

Warning

hcodes

H226

Hazard Classifications

Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk

WGK 2

flash_point_f

111.2 °F - closed cup

flash_point_c

44 °C - closed cup

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
SHBT3406
SHBR7427
SHBR6704
SHBQ7475
SHBR2407

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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
The preparation of tiglic and angelic acids and esters1.
Buckles RE and Mock GV.
The Journal of Organic Chemistry, 15(3), 680-684 (1950)
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
Aggregation pheromones in five taxa of the Drosophila virilis species group.
Bartelt RJ, et al.
Physiological Entomology, 11(4), 367-376 (1986)
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