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PHORBOL

PHORBOL Structure
CAS No.
17673-25-5
Chemical Name:
PHORBOL
Synonyms
PHORBOL;Phorbol >99%;Phorbol, >96%;4-beta-phorbol;phorbol white powder;phorbol practical grade;6,8-alpha-tetramethyl-l)-1;in stock Phorbol 17673-25-5;4abeta,7aalpha,7balpha,8alpha,9beta,9aalpha))-et;4,9,12-beta,13,20-pentahydroxy-1,6-tigliadien-3-on
CBNumber:
CB0741431
Molecular Formula:
C20H28O6
Molecular Weight:
364.43
MOL File:
17673-25-5.mol
Modify Date:
2024/3/5 13:46:46

PHORBOL Properties

Melting point 162-163° and 233-234°; mp 249-250°
alpha D24 +102° (water); D20 +118° (c = 0.4 in dioxane)
Boiling point 415.62°C (rough estimate)
Density 1.4
refractive index 1.4450 (estimate)
storage temp. Sealed in dry,Store in freezer, under -20°C
Water Solubility Soluble in water
solubility DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: slightly soluble; PBS (pH 7.2): 1 mg/ml
form powder to crystal
pka 11.36±0.70(Predicted)
color 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
CAS DataBase Reference 17673-25-5
EPA Substance Registry System Phorbol (17673-25-5)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H315-H319
Precautionary statements  P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
Hazard Codes  T+
Risk Statements  26/27/28-36/37/38
Safety Statements  26-27-36/37/39-45-28
RIDADR  UN 2811 6.1/PG 3
WGK Germany  3
RTECS  GZ0600000
HazardClass  6.1(b)
PackingGroup  III
HS Code  29062990
NFPA 704
0
4 0

PHORBOL price More Price(2)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
TCI Chemicals (India) P2732 Phorbol 17673-25-5 5MG ₹5600 2022-05-26 Buy
TCI Chemicals (India) P2732 Phorbol 17673-25-5 25MG ₹21900 2022-05-26 Buy
Product number Packaging Price Buy
P2732 5MG ₹5600 Buy
P2732 25MG ₹21900 Buy

PHORBOL Chemical Properties,Uses,Production

Description

Phorbol 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.

Uses

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

Definition

ChEBI: 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.

Preparation

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%.

General Description

White solid.

Air & Water Reactions

Water soluble.

Reactivity Profile

PHORBOL is unstable to prolonged exposure to air, light and ambient temperatures. PHORBOL is also sensitive to acid and alkalis and is subject to autooxidation. PHORBOL dissolves slowly, therefore solution in a desired solvent is best accomplished by prolonged shaking under an inert atmosphere. .

Fire Hazard

PHORBOL is probably combustible.

Toxicology

Toxicity of Phorbol: Dermal (mouse) LD50: 36 mg - mild, Unlike its diesters, phorbol does not appear to be a co-carcinogen or to enhance chemical mutagenesis. Evidence of carcinogenicity is limited. Highly toxic by inhalation, in contact with skin and if swallowed. Irritating to eyes, respiratory system and skin.

References

[1] JIE-PING FAN. Biphasic alcoholysis coupled with high-speed countercurrent chromatography for high performance on separating phorbol from Croton tiglium Linn extracts[J]. Journal of separation science, 2023. DOI:10.1002/jssc.202200984.

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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-one,1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-5h-cyclopropa( 4,9,12-beta,13,20-pentahydroxy-1,6-tigliadien-3-on 4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,6,8-tetramethyl-,(1ar-(1aalpha,1b 4abeta,7aalpha,7balpha,8alpha,9beta,9aalpha))-et 4-beta-phorbol 5h-cyclopropa(3,4)benz(1,2-e)azulen-5-one,1,1aalpha,1bbeta,4,4a,7aalpha,7b,8,9 5h-cyclopropa(3,4)benz(1,2-e)azulen-5-one,1,1a-beta,1b-alpha,4,4a,7a-beta,7b,8 6,8-alpha-tetramethyl-l)-1 phorbol practical grade phorbol white powder 4β,9α,12β,13α,20-Pentahydroxytiglia-1,6-dien-3-one 1,1aα,1bβ,4,4a,7aα,7b,8,9,9a-Decahydro-4aβ,7bα,9β,9aα-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8α-tetramethyl-5H-cyclopropa[3,4]benz[1,2-e]azulen-5-one Phorbol >99% (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b,9,9a-tetrahydroxy-3-(hydroxyMethyl)-1,1,6,8-tetraMethyl-1b,4,4a,7a,7b,8,9,9a-octahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-5(1aH)-one Phorbol, >96% 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)- High Purity Plant Extract Phorbol 17673-25-5 White Powder in stock Phorbol 17673-25-5 (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,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 17673-25-5 Diterpenoids Building block