phorbol

Chemical compound

Chemical compoundtype of chemical entityQ2705359

Also known as 4,9,12beta,13,20-pentahydroxytiglia-1,6-dien-3-one · 4,9,12beta,13,20-pentahydroxy-1,6-tigliadien-3-on

Formula: C₂₀H₂₈O₆
1
Sources
1.Stated in PubChem“PHORBOL”Retrieved 2016-10-05
View statement on Wikidata ↗
Mass: 364.1886 Da
1
Sources
1.Stated in PubChem“PHORBOL”Retrieved 2016-10-05
View statement on Wikidata ↗
Density: 1.415 g/cm³

Overview

From Wikipedia, the free encyclopedia · Read full article · Text CC BY-SA 4.0

Phorbol is a natural, plant-derived organic compound. It is a member of the tigliane family of diterpenes. Phorbol was first isolated in 1934 via the hydrolysis of croton oil, which is derived from the seeds of the purging croton, Croton tiglium. The structure of phorbol was determined in 1967. Various esters of phorbol 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 and potent phorbol ester is 12-O-tetradecanoylphorbol-13-acetate (TPA), also called phorbol-12-myristate-13-acetate (PMA), which is used as a biomedical research tool in contexts such as models of carcinogenesis.

Overview

Chemistry

Computed by PubChem CID 442070 (NIH) · Public domain

Molecular formula: C20H28O6
Molecular weight: 364.4 g/mol
IUPAC name: (1S,2S,6R,10S,11R,13S,14R,15R)-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
SMILES: C[C@@H]1[C@H]([C@@]2([C@@H](C2(C)C)[C@H]3[C@]1([C@@H]4C=C(C(=O)[C@]4(CC(=C3)CO)O)C)O)O)O
InChIKey: QGVLYPPODPLXMB-UBTYZVCOSA-N
XLogP: -0.8
Topological polar surface area: 118 Å²
H-bond donors / acceptors: 5 / 6
Complexity: 753

Chemistry

All data

44 statements · 64% with external sources · numbers in brackets are citations

Decomposition point: 250°C
1
Sources
1.Stated in CRC Handbook of Chemistry and Physics (95th edition)
View statement on Wikidata ↗
Canonical SMILES: CC1C(C2(C(C2(C)C)C3C1(C4C=C(C(=O)C4(CC(=C3)CO)O)C)O)O)O
1
Sources
1.Stated in PubChem“PHORBOL”Retrieved 2016-10-05
View statement on Wikidata ↗
Isomeric SMILES: C[C@@H]1[C@H]([C@@]2([C@@H](C2(C)C)[C@H]3[C@]1([C@@H]4C=C(C(=O)[C@]4(CC(=C3)CO)O)C)O)O)O
1
Sources
1.Stated in PubChem“PHORBOL”Retrieved 2016-10-05
View statement on Wikidata ↗
Subject has role: carcinogen
1
Sources
1.Stated in Medical Subject HeadingsRetrieved 2018-03-15
View statement on Wikidata ↗
Stereoisomer of: LSM-19043
Found in taxon: Gnidia chrysantha
1
Sources
1.Stated in Screening of thymelaeaceae species for irritant, cocarcinogenic and antineoplastic activity
View statement on Wikidata ↗
Croton tiglium
2
Sources
1.Stated in New phorbol and deoxyphorbol esters: isolation and relative potencies in inducing platelet aggregation and erythema of skin
2.Stated in Über den Giftstoff des Crotonöles. V. Die Gewinnung von Crotonharz, Dünnem Öl und Phorbol aus dem Crotonöl durch Alkoholyse
View statement on Wikidata ↗
Euphorbia tirucalli
1
Sources
1.Stated in On the Active Principles of the Spurge Family (Euphorbiaceae) XI. [1] The Skin Irritant and Tumor Promoting Diterpene Esters of Euphorbia tirucalli L. Originating from South Africa
View statement on Wikidata ↗
Rehmannia glutinosa
1
Sources
1.Stated in Identification of Autotoxic Compounds in Fibrous Roots of Rehmannia (Rehmannia glutinosa Libosch.)
View statement on Wikidata ↗
Refractive index: 1.648
Flash point: 313.8°C
Subclass of: tigliane diterpenoid

On other databases

27 identifiers linking phorbol across the web's reference databases

Data quality

statements

64%

externally sourced

Source last edited November 1, 2026. AIDb refreshes this page daily.

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AIDb. (2026). phorbol (Q2705359). Retrieved from https://aidb.si/e/phorbol-Q2705359