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W259306

Sigma-Aldrich

Indole

≥99%, FG

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Synonym(s):
1H-Benzo[b]pyrrole
Empirical Formula (Hill Notation):
C8H7N
CAS Number:
120-72-9
Molecular Weight:
117.15
FEMA Number:
2593
Beilstein:
107693
EC Number:
204-420-7
Council of Europe no.:
560
MDL number:
MFCD00005607
PubChem Substance ID:
24901173
Flavis number:
14.007
NACRES:
NA.21

biological source

synthetic

Quality Level

400

grade

FG
Fragrance grade
Kosher

Agency

follows IFRA guidelines
meets purity specifications of JECFA

reg. compliance

EU Regulation 1223/2009
EU Regulation 1334/2008 & 178/2002
FDA 21 CFR 117
FDA 21 CFR 172.515

Assay

≥99%

impurities

≤250 ppm Hexane, residual (solvent)

bp

253-254 °C (lit.)

mp

51-54 °C (lit.)

application(s)

flavors and fragrances

Documentation

see Safety & Documentation for available documents

food allergen

no known allergens

fragrance allergen

no known allergens

Organoleptic

pungent; floral; animal

SMILES string

c1ccc2[nH]ccc2c1

InChI

1S/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H

InChI key

SIKJAQJRHWYJAI-UHFFFAOYSA-N

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General description

Indole is one of the main flavor constituents of green tea.

Biochem/physiol Actions

Taste at 0.3-2 ppm

Other Notes

Natural occurrence: Burley tobacco, butter, coffee, dried bonito, egg, fish, malt, rum, tea, and wine.

Pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

Signal Word

Danger

Hazard Statements

H302 - H311 - H319 - H400

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Aquatic Acute 1 - Eye Irrit. 2

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 1

Flash Point(F)

249.8 °F - closed cup

Flash Point(C)

121 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Further Investigation of Flavor Constituents in Manufactured Green Tea
Yamanishi T, et al.
Agricultural and Biological Chemistry, 34(4), 599-608 (1970)
Facile access to 3-acylindoles through palladium-catalyzed addition of indoles to nitriles: the one-pot synthesis of indenoindolones.
Yuanhong Ma et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 19(4), 1189-1193 (2012-12-15)
Total synthesis of the tremorgenic indole diterpene paspalinine.
Masaru Enomoto et al.
Angewandte Chemie (International ed. in English), 51(51), 12833-12836 (2012-11-09)
Xueqing Geng et al.
The Plant cell, 24(11), 4763-4774 (2012-12-04)
The phytotoxin coronatine (COR) promotes various aspects of Pseudomonas syringae virulence, including invasion through stomata, growth in the apoplast, and induction of disease symptoms. COR is a structural mimic of active jasmonic acid (JA) conjugates. Known activities of COR are
Hélène Gérard et al.
The Journal of organic chemistry, 78(18), 9233-9242 (2013-08-07)
The chemo-, regio-, and stereoselectivities of multicomponent [4 + 2]/[3 + 2] domino cycloaddition reactions involving nitroindole derivatives with vinylethers and acrylates are studied computationnally and compared to experimental results. In this process, the nitroarene first reacts as an electron-deficient
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