17673-25-5

Basic information

• Product Name: PHORBOL
• Synonyms: 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
• CAS NO: 17673-25-5
• Molecular Formula: C₂₀H₂₈O₆
• Molecular Weight: 364.43
• Product Categories: Building block;Diterpenoids
• Mol File: 17673-25-5.mol

Chemical Properties

• Melting Point: 162-163° and 233-234°; mp 249-250°
• Boiling Point: 415.62°C (rough estimate)
• Flash Point: 313.8 °C
• Appearance: /
• Density: 1.4
• Vapor Pressure: 1.83E-15mmHg at 25°C
• Refractive Index: 1.4450 (estimate)
• Storage Temp.: −20°C
• PKA: 11.36±0.70(Predicted)
• Water Solubility: Soluble in water
• CAS DataBase Reference: PHORBOL(CAS DataBase Reference)
• NIST Chemistry Reference: PHORBOL(17673-25-5)
• EPA Substance Registry System: PHORBOL(17673-25-5)

Safety Data

• Hazard Codes: T+
• 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
• Hazardous Substances Data: 17673-25-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
PHORBOL is used as a starting material for the semisynthesis of various phorbol diesters, which are structurally analogous to diacylglycerol. These diesters activate PKC isoforms by associating with their C1 domains, making them valuable in the development of pharmaceutical compounds.
Used in Research and Development:
PHORBOL is used as a research tool in the study of protein kinase C and its role in various cellular processes. Its ability to activate PKC isoforms makes it a useful compound for understanding the mechanisms of cellular signaling and the development of potential therapeutic agents.
Used in Cancer Research:
PHORBOL exhibits tumor-promoting activities through the activation of protein kinase C. As a result, it is used in cancer research to study the mechanisms behind tumor promotion and to develop strategies for cancer prevention and treatment.

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.

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

Upstream product

• 1453222-03-1 (1aR,1bR,2R,3R,7bR,8R,9aR)-2-((tert-butyldimethylsilyl)oxy)-1,1,3,8-tetramethyl-7b-((trimethylsilyl)oxy)-1,1a,1b,2,3,5,7b,8,9,9a-decahydro-6H-cyclopropa[3,4]benzo[1,2-e]azulen-6-one 
• 41621-85-6 Phorbol 13,20-diacetate 
• 59-05-2 N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamic acid 

Downstream Products

• 37558-16-0 phorbol 12,13-dibutyrate 
• 82400-03-1 phorbol-20-trityl ether 
• 19891-06-6 Phorbol-12,13,20-tribenzoate 
• 19891-05-5 phorbol 12,13,20-triacetate 
• 41621-85-6 Phorbol 13,20-diacetate 
• 325781-13-3 Butyric acid (1aR,1bS,4aR,5S,7aS,7bS,8R,9S,9aS)-9-butyryloxy-4a,5,7b-trihydroxy-1,1,6,8-tetramethyl-3-trityloxymethyl-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester 
• 325781-14-4 Butyric acid (1aR,1bS,4aR,7aS,7bS,8R,9S,9aS)-9-butyryloxy-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5-oxo-3-trityloxymethyl-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester 
• 325781-12-2 Butyric acid (1aR,1bS,4aR,5S,7aS,7bS,8R,9S,9aS)-4a,5,7b,9-tetrahydroxy-1,1,6,8-tetramethyl-3-trityloxymethyl-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester 
• 325781-10-0 Butyric acid (1aR,1bS,4aR,7aS,7bR,8S,9aS)-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5,9-dioxo-3-trityloxymethyl-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester 
• 325781-09-7 Butyric acid (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-4a,7b,9-trihydroxy-1,1,6,8-tetramethyl-5-oxo-3-trityloxymethyl-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester 
• 325781-11-1 Butyric acid (1aR,1bS,4aR,5S,7aS,7bR,8S,9aS)-4a,5,7b-trihydroxy-1,1,6,8-tetramethyl-9-oxo-3-trityloxymethyl-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl ester 
• 37558-16-0 12-epi-phorbol-12,13-dibutyrate 
• 19891-08-8 Phorbol-17-<4-brom-benzoat> 
• 37558-16-0 phorbol 12,13-dibutyrate 

Relevant articles and documents

Phorbol Rearrangements

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.

Nineteen-step total synthesis of (+)-phorbol

Phorbol, the flagship member of the tigliane diterpene family, has been known for over 80 years and has attracted attention from many chemists and biologists owing to its intriguing chemical structure and the medicinal potential of phorbol esters. Access to useful quantities of phorbol and related analogues has relied on isolation from natural sources and semisynthesis. Despite efforts spanning 40 years, chemical synthesis has been unable to compete with these strategies, owing to its complexity and unusual placement of oxygen atoms. Purely synthetic enantiopure phorbol has remained elusive, and biological synthesis has not led to even the simplest members of this terpene family. Recently, the chemical syntheses of eudesmanes, germacrenes, taxanes and ingenanes have all benefited from a strategy inspired by the logic of two-phase terpene biosynthesis in which powerful C-C bond constructions and C-H bond oxidations go hand in hand. Here we implement a two-phase terpene synthesis strategy to achieve enantiospecific total synthesis of (+)-phorbol in only 19 steps from the abundant monoterpene (+)-3-carene. The purpose of this synthesis route is not to displace isolation or semisynthesis as a means of generating the natural product per se, but rather to enable access to analogues containing unique placements of oxygen atoms that are otherwise inaccessible.

Bioactive constituents from the leaves of Croton tiglium

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

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.

PROSTRATIN ANALOGS, BRYOSTATIN ANALOGS, PRODRUGS, SYNTHETIC METHODS, AND METHODS OF USE

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.

Methods for the selective expansion of lymphocytes by in vitro cultivation

The invention is directed to methods for the production of selected populations of lymphocytes. Lymphocytes produced can be isolated and purified using well known and established procedures to provide a consistent lymphocyte source which one of ordinary skill in the art can modify to provide an appropriate type or an optimal level of a desired lymphocyte. The availability of such cell populations allows for not only for the complete reconstitution of the depleted, defective or missing lymphocyte population in a patient, but also provides the flexibility of having sufficient cells to permit multiple or cyclic treatments. These methods for expanding target cell populations are broadly applicable to the selective expansion of several types of lymphocytes and are demonstrated to maintain phenotype as well as antigen specificity.

Phorbol derivatives having antivirus activity

An antiviral agent comprising as an active ingredient a phorbol derivative of formula (I): (wherein R1, R2, R3, R4, and R5, independently one another, represent a hydrogen atom, an aliphatic carboxylic acid residue, or an aromatic carboxylic acid residue) having a ratio r=CC0/IC100, i.e., ratio of concentration CC0at which survival of MT-4 cells is decreased upon cell proliferation tests to concentration IC100at which HIV-1-induced cytopathic effect (CPE) on MT-4 cells is inhibited by 100%, of 2 or more and having a protein kinase C(PKC) activation of 30% or less at a concentration of 10 ng/mL. The agent is useful as an anti-HIV agent.

Peptide fragments of tissue plasminogen activator

Novel peptide fragments of tissue plasminogen activator are described which have activity for inhibiting (a) the binding of tPA to human endothelial cells, and (b) the inactivation of tPA by plasminogen activator inhibitor-1 (PAI-1). Six peptides or peptide amides with these activities have the sequences, numbered according to the native protein: tPA (31-55), tPA (81-105), tPA (181-205), tPA (301-325), tPA (451-475, and tPA (531-555). It is hoped that small, synthesizeable molecules which prevent the inactivation of tPA by PAI-1 may provide a means for improving the efficacy of therapeutically administered tPA or for reducing the tendency of patients with elevated plasma PAI-1 concentrations to form fibrin clots.