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포르볼

5H-Cyclopropa[3,4]benz[1,2-e]azulen-5-one,1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-,(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-

HCID 290670
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
17673-25-5
표준 SMILES
CC1=CC2C(O)(CC(CO)=CC3C4C(C)(C)C4(O)C(O)C(C)C32O)C1=O
InChIKey
QGVLYPPODPLXMB-UHFFFAOYSA-N
분자식
C20H28O6
평균 분자량
364.4 g/mol
단동위원소 질량
364.18858861

개요

See also: Phorbol (annotation moved to); 4alpha-Phorbol (annotation moved to).

이름 및 식별자

우선 이름
5H-Cyclopropa[3,4]benz[1,2-e]azulen-5-one,1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-,(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-
IUPAC
1,6,13,14-tetrahydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyltetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dien-5-one
현지명
포르볼
영어명
PHORBOL
분자식
C20H28O6
분자량
364.43

이름 및 동의어

4-alpha-PHR4-PhorbolNSC1547785H-Cyclopropa[3,4]benz[1,2-e]azulen-5-one,1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-,(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-PhorbolPhorbol4.b.-Phorbol4-.beta.-Phorboltetrahydroxy-(hydroxymethyl)-tetramethyl-[?]onePhorbol [M+H]+SCHEMBL3403135(1S,2S,6R,10S,11R,13S,14R,15R)-1,6,13,14-tetrahydroxy-8-(hydroxymethyQGVLYPPODPLXMB-UHFFFAOYSA-N
이름 더 보기
포르볼PHORBOLPhorbol >99%Phorbol, >96%4-beta-phorbolPhorbol (6CI, 7CI)phorbol white powderPhorbol, 10 mM in DMSOphorbol practical grade6,8-alpha-tetramethyl-l)-1in stock Phorbol 17673-25-5
AKOS030254824SMP2_000315DB-044269DB-0469084 beta,9alpha,12 beta,13alpha,20-Pentahydroxy- tiglia-1,6-dien-3-one1,6,13,14-tetrahydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dien-5-one4a,7b,9,9a-Tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-5H-cyclopropa[3,4]benzo[1,2-E]azulen-5-one #4BETA,9ALPHA,12BETA,13ALPHA,20-PENTAHYDROXYTIGLIA-1,6-DIEN-3-ONE;PHORBOL;,9,9a-decahydro-4a-alpha,7b-alpha,9-beta,9a-alpha-tetrahydroxy-3-(hydroxymethy;,9a-decahydro-4abeta,7balpha,9beta,9aalpha-tetrahydroxy-3-(hydroxymethyl)-1,1,;4)benz(1,2-e)azulen-5-o

물성

구조 계산 물성

XLogP
-0.8
극성 표면적
118 Ų
수소 결합 공여자 수
5
수소 결합 수용자 수
6
회전 가능 결합 수
1
무거운 원자 수
26
형식 전하
0
복잡도
753

물리화학적 성질

녹는점
162 · 162-163° and 233-234°; mp 249-250°
끓는 점
415.62 °C · 415.62°C (rough estimate)
밀도
1.4 · 1.4
굴절률
1.445 · 1.4450 (estimate)
저장 조건
-20 °C · Sealed in dry,Store in freezer, under -20°C
수용성
물에 용해됨
용해도
30 mg/ml; · DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: slightly soluble; PBS (pH 7.2): 1 mg/ml
물리적 상태
powder to crystal
산도 계수 (pKa)
11.36 · 11.36±0.70(Predicted)
색상
White to Orange to Green
InChIKey
QGVLYPPODPLXMB-UBTYZVCOSA-N
SMILES
C1(=O)[C@]2(O)[C@]([H])([C@@]3(O)[C@H](C)[C@@H](O)[C@@]4(O)C(C)(C)[C@@]4([H])[C@]3([H])C=C(CO)C2)C=C1C
EPA
Phorbol (17673-25-5)

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

안전 데이터

wgk
3
rtecs
GZ0600000
ridadr
UN 2811 6.1/PG 3
HS 번호
29062990
risk_code
26/27/28-36/37/38
hazard_code
T+
safety_code
26-27-36/37/39-45-28
포장분류
III
위험 등급
6.1(b)
유해 물질 데이터
17673-25-5(Hazardous Substances Data)

화학 및 산업

응용 분야 · 3건

개요Phorbol is a diterpene originally isolated from croton oil. It is used as a starting material for the semisynthesis of various phorbol diesters, which are structurally analogous to diacylglycerol and activate PKC isoforms by associating with their C1 domains.

용도Phorbol is a plant-derived diterpene that exhibits various biological activities such as its role as tumor promoters through the activation of protein kinase C.

일반 설명White solid.

제조 방법 · 1건

Phorbol can be extracted from croton oil by two-phase alcoholysis and purified by high-speed counter-current chromatography[1]. The specific method is as follows:The optimized operation conditions of biphasic alcoholysis were a reaction time of 91 min, a temperature of 14°C, and a croton oil-methanol ratio of 1:30 (g:ml). The phorbol during the biphasic alcoholysis was 3.2-fold higher in content than that obtained in conventional monophasic alcoholysis. The optimized high-speed countercurrent chromatography method was using the ethyl acetate/n-butyl alcohol/water at 4.7:0.3:5 (v:v:v) with Na2SO4 at 0.36 g/10 ml as the solvent system, using the mobile phase flow rate of 2 ml/min, the revolution of 800 r/min, under which the retention of the stationary phase was achieved at 72.83%. The crystallized phorbol following high-speed countercurrent chromatography was obtained as high purity of 94%.

상·하류 제품 정보

상류 원료

메토트렉세이트

하류 제품

Bisdecanoic acid (1aR)-1aα,1bβ,4,4a,5,7aα,7b,8,9,9a-decahydro-3-(decanoyloxy)methyl-4aβ,7bα-dihydroxy-1,1,6,8α-tetramethyl-5-oxo-1H-cyclopropa[3,4]benz[1,2-e]azulene-9β,9aα-diyl ester

관련 반응

0건
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데이터베이스 식별자

CAS
17673-25-5
PubChem CID
290670

공급사93 곳

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추가 설명

정의ChEBI: A diterpenoid with the structure of tigliane hydroxylated at C-4, -9, -12(beta), -13 and -20, with an oxo group at C-3 and unsaturation at the 1- and 6-positions.