72715-02-7

Basic information

• Product Name: Ilicol
• Synonyms: Ilicol;4alphaH-Eudesm-11(13)-ene-4,12-diol;Ilicic alcohol
• CAS NO: 72715-02-7
• Molecular Formula: C₁₅H₂₆O₂
• Molecular Weight: 238.36574
• Product Categories: Sesquiterpenoids
• Mol File: 72715-02-7.mol
• Article Data: 0

Chemical Properties

• Melting Point: 134-135 °C
• Boiling Point: 350.9±25.0 °C(Predicted)
• Appearance: /
• Density: 1.029±0.06 g/cm3(Predicted)
• PKA: 14.78±0.10(Predicted)
• CAS DataBase Reference: Ilicol(CAS DataBase Reference)
• NIST Chemistry Reference: Ilicol(72715-02-7)
• EPA Substance Registry System: Ilicol(72715-02-7)

Safety Data

• Hazardous Substances Data: 72715-02-7(Hazardous Substances Data)

Usage

General Description

Ilicol is a chemical compound that belongs to the category of complexity within the class of organic compounds. It has a molecular formula of C27H30O16 and a molecular weight of 610.52 g/mol. Ilicol is a natural product isolated from the leaves of Ilex cornuta (Chinese Holly). Its biological activity includes antioxidant and anti-inflammatory properties, making it potentially useful in the development of pharmaceuticals and health products. Additionally, it has potential application in the food and beverage industry due to its reported health benefits. Further studies are needed to fully understand its mechanism of action and potential uses in various industries.

Synthetic route

4-hydroxy-11(13)-eudesmen-12-oic acid (4586-68-9) → (1R,4aR,7R,8aR)-decahydro-7-(3-hydroxyprop-1-en-2-yl)-1,4a-dimethylnaphthalen-1-ol (72715-02-7)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran

(1R,4aR,7R,8aR)-decahydro-7-(3-hydroxyprop-1-en-2-yl)-1,4a-dimethylnaphthalen-1-ol (72715-02-7) → 4α-hydroxyeudesm-11-en-12-al (72715-06-1)

Conditions	Yield
With jones reagent	87%
With chromium(VI) oxide; sulfuric acid In acetone
With Jones reagent

acetic anhydride (108-24-7) + (1R,4aR,7R,8aR)-decahydro-7-(3-hydroxyprop-1-en-2-yl)-1,4a-dimethylnaphthalen-1-ol (72715-02-7) → 12-acetoxy-4α-hydroxyeudesm-11(13)-ene (72715-07-2)

Conditions	Yield
With pyridine for 12h;

(1R,4aR,7R,8aR)-decahydro-7-(3-hydroxyprop-1-en-2-yl)-1,4a-dimethylnaphthalen-1-ol (72715-02-7) → Selinan-4α-ol (16641-46-6)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethyl acetate

(1R,4aR,7R,8aR)-decahydro-7-(3-hydroxyprop-1-en-2-yl)-1,4a-dimethylnaphthalen-1-ol (72715-02-7) → 2-((2R,4aR,8R,8aR)-4a,8-Dimethyl-8-trimethylsilanyloxy-decahydro-naphthalen-2-yl)-propenal

Conditions	Yield
Multi-step reaction with 2 steps 1: 87 percent / Jones reagent 2: 91 percent / HMDS / CH2Cl2 / 20 °C View Scheme

(1R,4aR,7R,8aR)-decahydro-7-(3-hydroxyprop-1-en-2-yl)-1,4a-dimethylnaphthalen-1-ol (72715-02-7) → Trifluoro-acetic acid (1R,4aR,7R,8aR)-7-(1-formyl-vinyl)-1,4a-dimethyl-decahydro-naphthalen-1-yl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: 87 percent / Jones reagent 2: 92 percent / pyridine; DMAP / 20 °C View Scheme

(1R,4aR,7R,8aR)-decahydro-7-(3-hydroxyprop-1-en-2-yl)-1,4a-dimethylnaphthalen-1-ol (72715-02-7) → β-costal (76497-23-9, 88564-53-8, 3650-40-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 87 percent / Jones reagent 2: 56 percent / POCl3; pyridine / -20 °C View Scheme

(1R,4aR,7R,8aR)-decahydro-7-(3-hydroxyprop-1-en-2-yl)-1,4a-dimethylnaphthalen-1-ol (72715-02-7) → iso-β-costal

Conditions	Yield
Multi-step reaction with 2 steps 1: 87 percent / Jones reagent 2: 93 percent / p-TsOH; MS 4A / benzene / 80 °C View Scheme

Upstream product

• 4586-68-9 4-hydroxy-11⁽¹³⁾-eudesmen-12-oic acid 

Downstream Products

• 76497-23-9 costal