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| CAS No.: | 17673-25-5 |
|---|---|
| Name: | PHORBOL |
| Article Data: | 13 |
| Molecular Structure: | |
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| Formula: | C20H28 O6 |
| Molecular Weight: | 364.439 |
| 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 |
| Density: | 1.415 g/cm3 |
| Melting Point: | 162-163° and 233-234°; mp 249-250° |
| Boiling Point: | 572 °C at 760 mmHg |
| Flash Point: | 313.8 °C |
| Solubility: | Soluble in water |
| Hazard Symbols: |
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| Risk Codes: | 26/27/28-36/37/38 |
| 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. |
| Transport Information: | UN 2811 6 |
| PSA: | 118.22000 |
| LogP: | -0.06990 |
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Chemistry
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
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.
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. .
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. |
Consensus Reports
EPA Genetic Toxicology Program.
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 .gif){kind=small}
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
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.