ChemicalBook
Chinese Japanese Germany Korea

Piperonyl aldehyde

Piperonyl aldehyde
Piperonyl aldehyde structure
CAS No.
120-57-0
Chemical Name:
Piperonyl aldehyde
Synonyms
Blue P;PIPERONAL;FEMA 2911;NSC 26826;PIPERINAL;pipweonal;piperoanol;HELIOTROPIN;Geliotropin;HELIOTROPINE
CBNumber:
CB3246225
Molecular Formula:
C8H6O3
Formula Weight:
150.13
MOL File:
120-57-0.mol

Piperonyl aldehyde Properties

Melting point:
35-39 °C(lit.)
Boiling point:
264 °C(lit.)
Density 
1.2645 (rough estimate)
vapor pressure 
1 mm Hg ( 87 °C)
FEMA 
2911 | PIPERONAL
refractive index 
1.4500 (estimate)
Flash point:
>230 °F
storage temp. 
Dark Room
solubility 
methanol: 0.1 g/mL, clear
Water Solubility 
Slightly soluble
Sensitive 
Air & Light Sensitive
Merck 
13,7556
JECFA Number
896
BRN 
131691
Stability:
Stable, but air and light sensitive. Combustible. Incompatible with strong oxidizing agents, bases.
CAS DataBase Reference
120-57-0(CAS DataBase Reference)
Substances Added to Food (formerly EAFUS)
PIPERONAL
FDA 21 CFR
182.60
EWG's Food Scores
1
FDA UNII
KE109YAK00
NIST Chemistry Reference
Piperonal(120-57-0)
EPA Substance Registry System
Piperonal (120-57-0)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Hazard Codes  Xi
Risk Statements  38-52/53
Safety Statements  61-24/25
WGK Germany  2
RTECS  TO1575000
8-10-23
TSCA  Yes
HS Code  29329300
Toxicity LD50 orally in rats: 2700 mg/kg (Hagan)

Piperonyl aldehyde price More Price(13)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich W291102 Piperonal ≥99%, FCC, FG 120-57-0 10 kg $715 2021-03-22 Buy
Sigma-Aldrich W291102 Piperonal ≥99%, FCC, FG 120-57-0 25kg-k $1500 2020-08-18 Buy
Sigma-Aldrich W291102 Piperonal ≥99%, FCC, FG 120-57-0 25 kg $1550 2021-03-22 Buy
Sigma-Aldrich W291102 Piperonal ≥99%, FCC, FG 120-57-0 50kg-k $2800 2020-08-18 Buy
Sigma-Aldrich W291102 Piperonal ≥99%, FCC, FG 120-57-0 50 kg $3080 2021-03-22 Buy

Piperonyl aldehyde Chemical Properties,Uses,Production

Chemical Properties

white crystalline solid

Chemical Properties

Piperonal has a sweet, flowery odor reminiscent of heliotrope and a bittersweet taste.

Chemical Properties

Heliotropin occurs in a number of essential oils, but only in low concentrations. It forms white crystals (mp 37°C) with a sweet, floral, slightly spicy, heliotrope-like odor.

Occurrence

Reported found in the essential oils of Robinia pseudo-acacia and Eryngium poterium; in the oils of Spirea ulmaria and of leaves of Doryphora sassafras; also reported found in Tahitian and Bourbon vanilla, camphor wood oil, violet flowers concrete and absolute, burley tobacco, rabbiteye blueberry, melon, pepper, cooked chicken, sherry and dill.

Uses

Piperonal is an impurity of Tadalafil (T004500). Tadalafil impurity A.

Uses

In perfumery, in cherry and vanilla flavors, in organic syntheses.

Definition

ChEBI: An arenecarbaldehyde that is 1,3-benzodioxole substituted by a formyl substituent at position 5. It has been isolated from Piper nigrum.

Preparation

Heliotropin is produced by two main routes:
1) From isosafrole: For many years, oxidative cleavage of isosafrole was the only route applicable on an industrial scale. Isosafrole [120-58-1] is obtained by isomerization from safrole [94-59-7], which can be isolated from (Chinese) sassafras oil . Examples of oxidants that give good yields of heliotropin are chromium(VI) salts, oxygen, and ozone.
This method is still used currently, but the destructive exploitation of sassafras trees in Southeast Asia has led to a strong decline in the availability of sassafras oil and thus of safrole/isosafrole.
2) From catechol: Several routes have recently been developed for the synthesis of heliotropin from catechol. In one such route, catechol is converted into 3,4-dihydroxymandelic acid with glyoxylic acid in an alkaline medium in the presence of aluminum oxide. 3,4-Dihydroxymandelic acid is oxidized to the corresponding keto acid (e.g., with copper-(II) oxide), which is decarboxylated to 3,4-dihydroxybenzaldehyde. The latter product is converted into heliotropin, for example, by reactionwith methylene chloride in the presence of quaternary ammonium salts.
In another route, catechol is first reacted with methylene chloride and converted into 1,2-methylenedioxybenzene . Reaction with glyoxylic acid in strongly acidic media yields 3,4-methylenedioxymandelic acid . Subsequent oxidation and decarboxylation with nitric acid afford heliotropin.
Alternative routes that start from 1,2-methylenedioxybenzene and use piperonyl chloride as intermediate have been described .

Aroma threshold values

Detection: 62 ppb to 1 ppm. Aroma characteristics at 1.0%: sweet, anise-like, almond vanilla, floral, black cherry pit, berry raspberry, powdery coumarin-like with a hint of hay.

Taste threshold values

Taste characteristics at 10 to 50 ppm: ripe black cherry fleshy, ripe berry, sweet, macaroon, Jordan almond, creamy vanilla, spicy cream soda, courmarin, slight floral with hay nuances.

Synthesis Reference(s)

Canadian Journal of Chemistry, 64, p. 225, 1986 DOI: 10.1139/v86-039
The Journal of Organic Chemistry, 48, p. 4053, 1983 DOI: 10.1021/jo00170a036
Tetrahedron Letters, 33, p. 5909, 1992 DOI: 10.1016/S0040-4039(00)61086-9

General Description

Colorless lustrous crystals.

Air & Water Reactions

Slightly water soluble .

Reactivity Profile

Piperonyl aldehyde is an aldehyde. Aldehydes are frequently involved in self-condensation or polymerization reactions. These reactions are exothermic; they are often catalyzed by acid. Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction). The addition of stabilizers (antioxidants) to shipments of aldehydes retards autoxidation. Piperonyl aldehyde is sensitive to light. Piperonyl aldehyde may react with oxidizing materials.

Fire Hazard

Flash point data for Piperonyl aldehyde are not available. Piperonyl aldehyde is probably combustible.

Safety Profile

Moderately toxic by ingestion and intraperitoneal routes. Can cause central nervous system depression. A human skin irritant. Mutation data reported. Combustible when exposed to heat or flame; can react with oxidizing materials. See also ALDEHYDES.

Chemical Synthesis

By the oxidation of isosafrole with potassium dichromate and sulfuric acid and subsequent steam distillation of piperonal

Metabolism

In the animal body heliotropin undergoes the expected metabolic reaction involving oxidation to the corresponding acid (Williams, 1959).

Purification Methods

Crystallise piperonal from aqueous 70% EtOH or EtOH/water. [Beilstein 19/4 V 225.]

Piperonyl aldehyde Preparation Products And Raw materials

Raw materials

Preparation Products


Piperonyl aldehyde Spectrum


120-57-0(Piperonyl aldehyde)Related Search:


Copyright 2017 © ChemicalBook. All rights reserved