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Phorbol

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Phorbol

EINECS N/A
CAS No. 17673-25-5 Density 1.415 g/cm3
PSA 118.22000 LogP -0.06990
Solubility Soluble in water Melting Point 162-163° and 233-234°; mp 249-250°
Formula C20H28 O6 Boiling Point 572 °C at 760 mmHg
Molecular Weight 364.439 Flash Point 313.8 °C
Transport Information UN 2811 6 Appearance N/A
Safety Experimental reproductive effects. A skin irritant. Questionable carcinogen with experimental carcinogenic and tumorigenic data. When heated to decomposition it emits acrid smoke and irritating fumes. See also PHORBOL ACETATE, LAURATE; PHORBOL-12,13-DIACETATE; PHORBOL-12,13-DIBENZOATE; PHORBOL-12,13-DIBUTYRATE; PHORBOL-12,13-DIDECANOATE; PHORBOL-12,13-DIHEXA(Δ-2,4)-DIENOATE; PHORBOL-12,13-DIHEXANOATE; PHORBOL 12,13-DIMYRISTATE; PHORBOL LAURATE, (+)-S-2-METHYL-BUTYRATE; PHORBOL MONOACETATE MONOLAURATE; PHORBOL MONODECANOATE (S)-(+)-MONO(2-METHYLBUTYRATE); (E)-PHORBOL MONODECANOATE MONO(2-METHYLCROTONATE); PHORBOL MYRISTATE ACETATE; PHORBOL-9-MYRISTATE-9a-ACETATE-3-ALDEHYDE; PHORBOLOL MYRISTATE ACETATE; PHORBOL-12-o-TIGLYL-13-BUTYRATE; PHORBOL-12-o-TIGLYL-13-DODECANOATE. Risk Codes 26/27/28-36/37/38
Molecular Structure Molecular Structure of 17673-25-5 (PHORBOL) Hazard Symbols
Synonyms

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-(1aa,1bb,4ab,7aa,7ba,8a,9b,9aa)]-; 5H-Cyclopropa[3,4]benz[1,2-e]azulen-5-one, 1,1aa,1bb,4,4a,7aa,7b,8,9,9a-decahydro-4ab,7ba,9b,9aa-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8a-tetramethyl-, (+)- (8CI); Phorbol (6CI,7CI); 4b-Phorbol; NSC 154778

Article Data 13

Phorbol Chemical Properties

Molecular Structure:


Molecular Formula: C20H28O6
Molecular Weight: 364.4327
Synonyms of Phorbol (CAS NO.17673-25-5): 1,1a,1b,4,4a,7a,7b,8,9,9a-Decahydro-4a,7b,9,9a-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5H-cyclopropa(3,4)benz(1,2-e)azulen-5-one (1aR-(1aalpha,1bbeta,4abeta,7aalpha,7balpha,8alpha,9beta,9aalpha))- ; 4,9,12-beta,13,20-Pentahydroxy-1,6-tigliadien-3-on ; 4-beta-Phorbol ; 4beta-Phorbol ; 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)-1,6,8-tetramethyl-, (1aR-(1aalpha,1beta,4abeta,7aalpha,7balpha,8alpha,9beta,9aalpha))- ; 5H-Cyclopropa(3,4)benz(1,2-e)azulen-5-one, 1,1aalpha,1bbeta,4,4a,7aalpha,7b,8,9,9a-decahydro-4abeta,7balpha,9beta,9a alpha-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8alpha-tetramethyl-, (+)- ; CCRIS 694 ; HSDB 4328 ; NSC 154778
CAS NO: 17673-25-5
Classification Code: Mutation data ; Natural Product ; Reproductive Effect ; Skin / Eye Irritant ; Tumor data 
Index of Refraction: 1.648
Molar Refractivity: 93.69 cm3
Molar Volume: 257.4 cm3
Surface Tension: 70.5 dyne/cm
Density: 1.415 g/cm3
Flash Point: 313.8 °C
Enthalpy of Vaporization: 98.49 kJ/mol
Boiling Point: 572 °C at 760 mmHg
Vapour Pressure: 1.83E-15 mmHg at 25°C

Phorbol Uses

Various esters of Phorbol (CAS NO.17673-25-5) have important biological properties, the most notable of which is the capacity to act as tumor promoters through activation of protein kinase C. They mimic diacylglycerols, glycerol derivatives in which two hydroxyl groups have reacted with fatty acids to form esters. The most common phorbol ester is 12-O-tetradecanoylphorbol-13-acetate (TPA), also called phorbol-12-myristate-13-acetate (PMA), which is used as biomedical research tool in models of carcinogenesis.
 

Phorbol Production

Reactivity Profile:  Phorbol (CAS NO.17673-25-5) 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. .
 

Phorbol Toxicity Data With Reference

1.    

skn-mus 36 mg MLD

    PLMEAA    Planta Medica. 22 (1972),241.
2.    

ipr-mus TDLo:400 mg/kg/25W:CAR

    CNREA8    Cancer Research. 30 (1970),2744.

Phorbol Consensus Reports

EPA Genetic Toxicology Program.

Phorbol Safety Profile

Experimental reproductive effects. A skin irritant. Questionable carcinogen with experimental carcinogenic and tumorigenic data. When heated to decomposition it emits acrid smoke and irritating fumes.
Safety Information of Phorbol (CAS NO.17673-25-5):
Hazard Codes: T+
T+: Very Toxic
Risk Statements: 26/27/28-36/37/38
26/27/28: Very Toxic by inhalation, in contact with skin and if swallowed 
36/37/38: Irritating to eyes, respiratory system and skin  
Safety Statements: 26-27-36/37/39-45-28
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
27: Take off immediately all contaminated clothing 
36/37/39: Wear suitable protective clothing, gloves and eye/face protection 
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) 
28: After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) 
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS: GZ0600000
HazardClass: 6.1(b)
PackingGroup: III

Phorbol Specification

 Phorbol (CAS NO.17673-25-5) is a natural, plant-derived organic compound. It is a member of the tigliane family of diterpenes. It was first isolated in 1934 as the hydrolysis product of croton oil, which is derived from the seeds of Croton tiglium. Phorbol's structure was determined in 1967 It is very soluble in most polar organic solvents, as well as in water.
 

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