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W291102

Sigma-Aldrich

Piperonal

≥99%, FCC, FG

Synonym(s):

1,3-Benzodioxole-5-carboxaldehyde, 3,4-(Methylenedioxy)benzaldehyde, Heliotropin

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About This Item

Empirical Formula (Hill Notation):
C8H6O3
CAS Number:
120-57-0
Molecular Weight:
150.13
FEMA Number:
2911
Beilstein/REAXYS Number:
131691
EC Number:
204-409-7
Council of Europe no.:
104
MDL number:
MFCD00005828
UNSPSC Code:
12164502
PubChem Substance ID:
24901389
Flavis number:
5.016
NACRES:
NA.21

biological source

synthetic

Quality Level

400

grade

FG
Fragrance grade
Halal
Kosher

agency

follows IFRA guidelines
meets purity specifications of JECFA

reg. compliance

EU Regulation 1223/2009
EU Regulation 1334/2008 & 178/2002
FCC
FDA 21 CFR 182.60

vapor pressure

1 mmHg ( 87 °C)

assay

≥99%

bp

264 °C (lit.)

mp

35-39 °C (lit.)

application(s)

flavors and fragrances

documentation

see Safety & Documentation for available documents

food allergen

no known allergens

fragrance allergen

heliotropine

organoleptic

cherry; sweet; vanilla

SMILES string

[H]C(=O)c1ccc2OCOc2c1

InChI

1S/C8H6O3/c9-4-6-1-2-7-8(3-6)11-5-10-7/h1-4H,5H2

InChI key

SATCULPHIDQDRE-UHFFFAOYSA-N

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Application


  • The synthesis and characterisation of MDMA derived from a catalytic oxidation of material isolated from black pepper reveals potential route specific impurities.: This study explores the synthesis and characterization of MDMA from piperonal, highlighting potential impurities unique to this synthesis route. This research has implications for forensic science and the identification of synthetic routes for MDMA (Plummer et al., 2016).

  • Design, synthesis, and biological evaluation of platensimycin analogues with varying degrees of molecular complexity.: This paper details the synthesis of platensimycin analogues using piperonal derivatives. The study evaluates the biological activities of these analogues, contributing to the development of new antibacterial agents (Nicolaou et al., 2008).

  • Synthesis and use of 4-peptidylhydrazido-N-hexyl-1,8-naphthalimides as fluorogenic histochemical substrates for dipeptidyl peptidase IV and tripeptidyl peptidase I.: This research presents the synthesis of piperonal-based substrates for histochemical applications, enabling the study of enzyme activities in biochemical assays (Ivanov et al., 2009).

Biochem/physiol Actions

Taste at 10-50 ppm

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H317

Hazard Classifications

Skin Sens. 1

wgk_germany

WGK 2

flash_point_f

150.1 °F

flash_point_c

65.62 °C

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The inhibition of rat nasal cytochrome P-450-dependent mono-oxygenase by the essence heliotropin (piperonal).
A R Dahl
Drug metabolism and disposition: the biological fate of chemicals, 10(5), 553-554 (1982-09-01)
J Sekizawa et al.
Mutation research, 101(2), 127-140 (1982-04-01)
The genotoxicity of safrole, 9 compounds that are structurally similar to safrole (anethole, cinnamaldehyde, cinnamyl alcohol, estragole, methyl eugenol, eugenol, isoeugenol, isosafrole, piperonal), 5 essential oils, cassia oil, cinnamon bark oil, clove oil, fennel oil) which contain the chemicals tested
Patricia Guerra-Diaz et al.
Analytical chemistry, 82(7), 2826-2835 (2010-03-09)
A preconcentration device that targets the volatile chemical signatures associated with illicit drugs and explosives (high and low) has been designed to fit in the inlet of an ion mobility spectrometer (IMS). This is the first reporting of a fast
S Peock et al.
Journal of the Royal Society of Health, 113(6), 292-294 (1993-12-01)
Piperonal, once used to kill lice in Australian hospitals, was acclaimed as an effective pediculicide (Corlette, 1925) by the standards of the day. It is unusual in also exhibiting a repellent action against lice, a property only recently realised. A
Ariel Ceferino Toloza et al.
Memorias do Instituto Oswaldo Cruz, 101(1), 55-56 (2006-05-16)
New alternative insecticides are necessary for the chemical control of head lice. In this study the fumigant knockdown time 50% (KT50) and repellency index (RI) of three aliphatic lactones was compared with two essential oils and DDVP, against permethrin-resistance Pediculus
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