469-83-0

Basic information

• Product Name: CAFESTOL
• Synonyms: CAFESTEROL;CAFESTOL;3bα,4,5,6,7,8,9,10,10aα,10b,11,12-Dodecahydro-7β-hydroxy-10bβ-methyl-5aβ,8β-methano-5aH-cyclohepta[5,6]naphtho[2,1-b]furan-7α-methanol;5A,8-Methano-5ah-cyclohepta(5,6)naphtho(2,1-B)furan-7-methanol, 3B,4,5,6,7,8,9,10,10A,10B,11,12-dodecahydro-7-hydroxy-10B-methyl-, (3bs-(3balpha,5abeta,7beta,8beta,10aalpha,10bbeta))-;5A,8-Methano-5ah-cyclohepta(5,6)naphtho(2,1-B)furan-7-methanol, 3B,4,5,6,7,8,9,10,10A,10B,11,12-dodecahydro-7-hydroxy-10B-methyl-, (3bs,5as,7R,8R,10ar,10bs)-;Ccris 1518;CAFESTOL(SH);(3bS,5aS,7R,8R,10aR,10bS)-3b,4,5,6,7,8,9,10,10a,10b,11,12-Dodecahydro-7-hydroxy-10b-methyl-5a,8-methano-5aH-cyclohepta[5,6]naphtho[2,1-b]furan-7-methanol
• CAS NO: 469-83-0
• Molecular Formula: C₂₀H₂₈O₃
• Molecular Weight: 316.43
• Product Categories: Di-Terpenoids
• Mol File: 469-83-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 160-162℃ (分解) (ethyl ether pentane )
• Boiling Point: 468.6 °C at 760 mmHg
• Flash Point: 237.2 °C
• Appearance: /
• Density: 1.23±0.1 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.604
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Soluble in dichlormethane, DMSO or ethanol
• PKA: 14.44±0.40(Predicted)
• CAS DataBase Reference: CAFESTOL(CAS DataBase Reference)
• NIST Chemistry Reference: CAFESTOL(469-83-0)
• EPA Substance Registry System: CAFESTOL(469-83-0)

Safety Data

• RTECS: PB9185090
• Hazardous Substances Data: 469-83-0(Hazardous Substances Data)

Usage

Description

Cafestol is a diterpene molecule derived from coffee beans, known for its anti-carcinogenic properties and ability to induce glutathione S-transferase, a detoxifying enzyme in the body.

Uses

Used in Pharmaceutical Industry:
Cafestol is used as an anti-carcinogenic agent for its potential to combat cancer. Studies have shown that it can help in the prevention and treatment of various types of cancer by modulating cellular processes and reducing the risk of tumor growth.
Used in Health and Nutrition Industry:
Cafestol is used as a natural extract from coffee beans to induce glutathione S-transferase, which plays a crucial role in detoxification and protection against oxidative stress. This application can be beneficial for promoting overall health and well-being.

InChI:InChI=1/C20H28O3/c1-18-7-5-16-14(6-9-23-16)15(18)4-8-19-10-13(2-3-17(18)19)20(22,11-19)12-21/h6,9,13,15,17,21-22H,2-5,7-8,10-12H2,1H3/t13?,15-,17+,18-,19+,20+/m1/s1

Synthetic route

kahweol → cafestol (469-83-0)

Conditions	Yield
With ethanol; sodium
With ethanol; nickel Hydrogenation;

cafestol (469-83-0) + 4-chlorobenzoyl chloride (586-75-4) → C27H31BrO4

Conditions	Yield
With dmap In pyridine; dichloromethane at 20℃; for 4h;

cafestol (469-83-0) + acetic anhydride (108-24-7) → cafestol acetate (81760-48-7)

Conditions	Yield
With pyridine
With sodium acetate

cafestol (469-83-0) → (3bS)-10b-methyl-(3br,10ac,10bt)-Δ2,3a(12a)-dodecahydro-5at,8t-methano-cyclohepta[5,6]naphtho[2,1-b]furan-7-carbaldehyde

Conditions	Yield
With zinc at 190℃; under 0.01 Torr;
Multi-step reaction with 2 steps 1: sodium acetate 2: zinc-powder / 190 °C / 0.01 Torr View Scheme
With toluene; zinc

cafestol (469-83-0) → (3aR)-7t-Hydroxymethyl-10b-methyl-(3ar,3bt,10at,10bc,12ac)-hexadecahydro-5ac,8c-methano-cyclohepta[5,6]naphtho[2,1-b]furan-7c-ol (108665-09-4, 121960-32-5)

Conditions	Yield
With palladium on activated charcoal; ethanol Hydrogenation;

cafestol (469-83-0) → (4bS)-8c-acetoxymethyl-8t-hydroxy-11b-methyl-(4ar,11ac,11bt)-Δ4-tetradecahydro-3ξ,13aξ-epoxido-6at,9t-methano-cyclohepta[a]phenanthrene-1ξ,2ξ-dicarboxylic acid-anhydride

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine 2: benzene View Scheme

cafestol (469-83-0) → (3aS)-10B-methyl-(3ar,3bc,10ac,10bt,12ac)-tetradecahydro-5at,8t-methano-cyclohepta[5,6]naphtho[2,1-b]furan-7-one

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine 2: platinum; acetic acid / anschliessend Hydrolyse und Behandlung des Reaktionsprodukts mit Perjodsaeure in wss. Methanol View Scheme
Multi-step reaction with 2 steps 1: pyridine 2: platinum; acetic acid / Hydrogenation.anschliessend Hydrolyse und Behandlung des Reaktionsprodukts mit Perjodsaeure in wss. Methanol View Scheme

cafestol (469-83-0) → (3aS)-10b-methyl-(3ar,3bc,10ac,10bt,12ac)-tetradecahydro-5at,8t-methano-cyclohepta[5,6]naphtho[2,1-b]furan-7-one semicarbazone

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine 2: platinum; acetic acid / anschliessend Hydrolyse und Behandlung des Reaktionsprodukts mit Perjodsaeure in wss. Methanol View Scheme
Multi-step reaction with 3 steps 1: pyridine 2: platinum; acetic acid / Hydrogenation.anschliessend Hydrolyse und Behandlung des Reaktionsprodukts mit Perjodsaeure in wss. Methanol View Scheme

cafestol (469-83-0) → (3bS)-10b-methyl-(3br,10ac,10bt)-Δ2,3a(12a)-decahydro-5at,8t-methano-cyclohepta[5,6]naphtho[2,1-b]furan-7-one (108664-98-8)

Conditions	Yield
With lead(IV) acetate; benzene

cafestol (469-83-0) → (3bS)-10b-methyl-(3br,10ac,10bt)-Δ2,3a(12a)-decahydro-5at,8t-methano-cyclohepta[5,6]naphtho[2,1-b]furan-7-one semicarbazone

Conditions	Yield
Multi-step reaction with 2 steps 1: lead (IV)-acetate; benzene View Scheme

cafestol (469-83-0) → (4bS)-11b-methyl-8-oxo-(4br,11ac,11bt)-Δ4-tetradecahydro-3ξ,13aξ-epoxido-6at,9t-methano-cyclohepta[a]phenanthrene-1ξ,2ξ-dicarboxylic acid-anhydride

Conditions	Yield
Multi-step reaction with 2 steps 1: lead (IV)-acetate; benzene 2: benzene View Scheme

cafestol (469-83-0) → (3aR)-10b-methyl-(3ar,3bt,10at,10bc,12ac)-tetradecahydro-5ac,8c-methano-cyclohepta[5,6]naphtho[2,1-b]furan-7-one

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine 2: platinum; acetic acid / Hydrogenation.anschliessend Hydrolyse und Behandlung des Reaktionsprodukts mit Perjodsaeure in wss. Methanol View Scheme

cafestol (469-83-0) → (3aR)-7t-Acetoxymethyl-10b-methyl-(3ar,3bt,10at,10bc,12ac)-hexadecahydro-5ac,8c-methano-cyclohepta[5,6]naphtho[2,1-b]furan-7c-ol (108665-11-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine 2: palladium; ethanol / Hydrogenation View Scheme

cafestol (469-83-0) → ((4Z,4aS)-11b-methyl-3,8-dioxo-(4ar,11ac,11bt)-dodecahydro-6at,9t-methano-cyclohepta[a]naphthalen-4-yliden)-acetic acid

Conditions	Yield
With chromium(VI) oxide

maleic anhydride (108-31-6) + cafestol (469-83-0) → (4bS)-8t-hydroxy-8c-hydroxymethyl-11b-methyl-(4ar,11ac,11bt)-Δ4-tetradecahydro-3ξ,13aξ-epoxido-6at,9t-methano-cyclohepta[a]phenanthrene-1ξ,2ξ-dicarboxylic acid-anhydride

Conditions	Yield
With benzene

cafestol (469-83-0) + zinc → anhydrocafestol

Conditions	Yield
at 190℃; under 0.01 Torr;
at 190℃; under 0.01 Torr;

cafestol (469-83-0) + toluene (108-88-3) + zinc → anhydrocafestol

cafestol (469-83-0) + chromium (VI)-oxide + water containing acetic acid → hydroxy-oxo-norcafestenolide

pyridine (110-86-1) + monoperoxyphthalic acid (2311-91-3) + diethyl ether (60-29-7) + cafestol (469-83-0) + acetic anhydride (108-24-7) → diacetoxy-oxy-cafestenolide

Upstream product

• 76280-80-3 (1R,4aR,10aS)-7-Methoxy-4a-methyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-1-ol 
• 1424371-49-2 C₁₆H₂₂O₂ 
• 1589590-44-2 C₁₆H₂₄O₂ 
• 93782-92-4 (E)-6-iodo-5-methylhex-5-en-1-ol 
• 928-90-5 5-hexyl-1-ol 

Downstream Products

• 81760-48-7 cafestol acetate 

Relevant articles and documents

Total synthesis of (±)-cafestol: A late-stage construction of the furan ring inspired by a biosynthesis strategy

An efficient bioinspired approach to the total synthesis of (±)-cafestol features a late-stage installation of the furan ring with a mild Au-catalyzed cycloisomerization. The Et2AlCl-promoted aldehyde-ene cyclization and subsequent Friedel-Crafts reaction deliver a requisite tricyclic system in gram scale with high stereo- and regioselectivity. Moreover, a highly stereoselective SmI2-mediated aldehyde-alkene radical cyclization furnishes the key bicyclo[3.2.1]octane skeleton to offer an advanced intermediate for the synthesis of other oxygenated ent-kaurene diterpenoids.

Preparation of cafestol

A process for the preparation of cafestol from kahweol wherein the kahweol is hydrogenated in the presence of a partially deactivated palladium catalyst on a calcium carbonate or active carbon support conditioned by lead. A process for preparing a mixture of cafestol and kahweol by treating coffee oil with anhydrous methanol in the presence of a basic catalyst is also disclosed.