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Merck
CN

W291102

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
Council of Europe no.:
104
UNSPSC Code:
12164502
PubChem Substance ID:
24901389
Flavis number:
5.016
EC Number:
204-409-7
NACRES:
NA.21
MDL number:
MFCD00005828
Beilstein/REAXYS Number:
131691
Organoleptic:
cherry; sweet; vanilla
Grade:
FG, Fragrance grade, Halal, Kosher
Biological source:
synthetic
Agency:
follows IFRA guidelines, meets purity specifications of JECFA
Food allergen:
no known allergens

Key Documents

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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

biological source

synthetic

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

Quality Level

300, 400

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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

signalword

Warning

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

150.1 °F

flash_point_c

65.62 °C

ppe

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

pictograms

Health hazardExclamation mark
GHS08,GHS07

Hazard Classifications

Repr. 2 - Skin Sens. 1

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SHBQ6318
SHBQ5824
SHBQ2805
SHBN9277
SHBP5116

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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
A R Dahl et al.
Biochemical pharmacology, 34(5), 631-636 (1985-03-01)
Eighteen methylenedioxyphenyl (MDP) compounds, including some commonly inhaled by people, were tested for the ability to inhibit rabbit nasal microsomal cytochrome P-450-dependent hexamethylphosphoramide (HMPA) N-demethylase. For comparison, liver microsomes were also used. Nasal cytochrome P-450 from rabbits metabolized MDP compounds
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
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
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)
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