17673-25-5 Usage
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 17673-25-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,7,6,7 and 3 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 17673-25:
(7*1)+(6*7)+(5*6)+(4*7)+(3*3)+(2*2)+(1*5)=125
125 % 10 = 5
So 17673-25-5 is a valid CAS Registry Number.
InChI:InChI=1/C20H28O6/c1-9-5-13-18(24,15(9)22)7-11(8-21)6-12-14-17(3,4)20(14,26)16(23)10(2)19(12,13)25/h5-6,10,12-14,16,21,23-26H,7-8H2,1-4H3
17673-25-5Relevant articles and documents
Phorbol Rearrangements
Zimmermann, Tomas,Franzyk, Henrik,Christensen, S?ren Br?gger
, p. 2134 - 2137 (2018)
An alternative procedure for isolation of 4β-phorbol from seeds of Croton tiglium has been developed, and an artifact containing a furan ring formed by rearrangement of 12,13,20-O-triacylated phorbol derivatives into (6bS,7R,8R,8aS)-2-(hydroxymethyl)-5,7,9,9-tetramethyl-3,7,8,9,9a,9b-hexahydrocyclopropa[3′,4′]benzo[1′,2′:3,4]cyclohepta[1,2-b]furan-6b,8,8a-triol (8a) has been characterized. A mechanism involving an oxidative rearrangement and a decarboxylation for formation of the artifact is proposed.
Bioactive constituents from the leaves of Croton tiglium
Duan, Li-Kun,Feng, Jin-E.,He, Hong-Ping,Huang, Chun-Qiu,Jiang, Zhi-Yong,Li, Xiao-Fei,Li, Yuan,Liu, Chun-Jiang,Shi, Sheng-Li,Zuo, Ai-Xue
, p. 65 - 72 (2022/03/15)
Fifteen compounds, including five new phorbol esters (1-5) and ten known metabolites were isolated from the leaves of Croton tiglium. The structures of new compounds 1-5 were determined by comprehensive analysis of the HRESIMS, IR, 1D and 2D NMR spectral
PROSTRATIN ANALOGS, BRYOSTATIN ANALOGS, PRODRUGS, SYNTHETIC METHODS, AND METHODS OF USE
-
, (2011/02/18)
Embodiments of the present disclosure provide for prostratin analogs, bryostatin analogs, prodrugs of prostratin and prostratin analogs, methods of making prostratin analogs, and methods of making prodrugs of prostratin and prostratin analogs, methods of use of prostratin analogs, bryostatin analogs, and prodrugs thereof, and the like.
