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헤리오트로핀

헤리오트로핀
헤리오트로핀 구조식 이미지
카스 번호:
120-57-0
한글명:
헤리오트로핀
동의어(한글):
디옥시에틸렌프로트카테큐알데히드;피페로날;헤리오트로핀;헬리오트로핀
상품명:
Piperonyl aldehyde
동의어(영문):
Blue P;PIPERONAL;FEMA 2911;NSC 26826;PIPERINAL;pipweonal;piperoanol;HELIOTROPIN;Geliotropin;HELIOTROPINE
CBNumber:
CB3246225
분자식:
C8H6O3
포뮬러 무게:
150.13
MOL 파일:
120-57-0.mol

헤리오트로핀 속성

녹는점
35-39 °C(lit.)
끓는 점
264 °C(lit.)
밀도
1.2645 (rough estimate)
증기압
1 mm Hg ( 87 °C)
굴절률
1.4500 (estimate)
FEMA
2911 | PIPERONAL
인화점
>230 °F
저장 조건
Dark Room
용해도
methanol: 0.1 g/mL, clear
수용성
Slightly soluble
감도
Air & Light Sensitive
Merck
13,7556
JECFA Number
896
BRN
131691
안정성
Stable, but air and light sensitive. Combustible. Incompatible with strong oxidizing agents, bases.
CAS 데이터베이스
120-57-0(CAS DataBase Reference)
NIST
Piperonal(120-57-0)
EPA
Piperonal (120-57-0)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 Xi
위험 카페고리 넘버 38-52/53
안전지침서 61-24/25
WGK 독일 2
RTECS 번호 TO1575000
F 고인화성물질 8-10-23
TSCA Yes
HS 번호 29329300
유해 물질 데이터 120-57-0(Hazardous Substances Data)
독성 LD50 orally in rats: 2700 mg/kg (Hagan)
기존화학 물질 KE-02692
그림문자(GHS):
신호 어: Warning
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H315 피부에 자극을 일으킴 피부부식성 또는 자극성물질 구분 2 경고 P264, P280, P302+P352, P321,P332+P313, P362
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 P264, P280, P305+P351+P338,P337+P313P
H335 호흡 자극성을 일으킬 수 있음 특정 표적장기 독성 - 1회 노출;호흡기계 자극 구분 3 경고
예방조치문구:
P261 분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.
P304+P340 흡입하면 신선한 공기가 있는 곳으로 옮기고 호흡하기 쉬운 자세로 안정을 취하시오.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.
P405 밀봉하여 저장하시오.

헤리오트로핀 C화학적 특성, 용도, 생산

화학적 성질

white crystalline solid

화학적 성질

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

화학적 성질

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.

출처

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.

용도

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

용도

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

정의

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

제조 방법

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

일반 설명

Colorless lustrous crystals.

공기와 물의 반응

Slightly water soluble .

반응 프로필

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.

화재위험

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

신진 대사

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.]

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