2761-77-5

Basic information

• Product Name: 8(17),12,14-Labdatriene-19-oic acid
• Synonyms: (+)-Communic acid;(1S,4aα)-Decahydro-1β-(3-methyl-2,4-pentadienyl)-2-methylene-5,8aβ-dimethylnaphthalene-5β-carboxylic acid;(1S,8aα)-Decahydro-1α,4aβ-dimethyl-6-methylene-5β-(3-methyl-2,4-pentadienyl)naphthalene-1β-carboxylic acid;(8aα)-1,4aβ-Dimethyl-5β-(3-methyl-2,4-pentadienyl)-6-methylenedecalin-1β-carboxylic acid;8(17),12,14-Labdatriene-19-oic acid;Communic acid
• CAS NO: 2761-77-5
• Molecular Formula: C₂₀H₃₀O₂
• Molecular Weight: 302.45
• Mol File: 2761-77-5.mol
• Article Data: 0

Chemical Properties

• Melting Point: 121 °C
• Boiling Point: 414.0±34.0 °C(Predicted)
• Appearance: /
• Density: 1.00±0.1 g/cm3(Predicted)
• PKA: 4.67±0.60(Predicted)
• CAS DataBase Reference: 8(17),12,14-Labdatriene-19-oic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 8(17),12,14-Labdatriene-19-oic acid(2761-77-5)
• EPA Substance Registry System: 8(17),12,14-Labdatriene-19-oic acid(2761-77-5)

Safety Data

• Hazardous Substances Data: 2761-77-5(Hazardous Substances Data)

Usage

Description

8(17),12,14-Labdatriene-19-oic acid is a naturally occurring organic compound that belongs to the labdane family of diterpenoids. It is characterized by its unique chemical structure, featuring three double bonds and a carboxylic acid functional group. 8(17),12,14-Labdatriene-19-oic acid is known for its potential biological activities and applications in various fields.

Uses

Used in Pharmaceutical Industry:
8(17),12,14-Labdatriene-19-oic acid is used as a pharmaceutical compound for its potential therapeutic properties. It has been found to exhibit anti-inflammatory, antifungal, and antimicrobial activities, making it a promising candidate for the development of new drugs to treat various diseases and infections.
Used in Cosmetic Industry:
In the cosmetic industry, 8(17),12,14-Labdatriene-19-oic acid is used as an active ingredient in skincare products due to its potential anti-aging and skin-soothing properties. Its ability to modulate skin cell functions and reduce inflammation may contribute to improved skin health and appearance.
Used in Traditional Medicine:
8(17),12,14-Labdatriene-19-oic acid is also used in traditional medicine, particularly by indigenous peoples, for its medicinal properties. It is often extracted from plants like the common juniper (Juniperus communis) and is known for its anti-mycobacterial activity, which can be beneficial in treating certain bacterial infections.
Used in Drug Delivery Systems:
Similar to gallotannin, 8(17),12,14-Labdatriene-19-oic acid can be incorporated into novel drug delivery systems to enhance its applications and efficacy. By using various organic and metallic nanoparticles as carriers, the delivery, bioavailability, and therapeutic outcomes of this compound can be improved, potentially leading to more effective treatments for various conditions.

Synthetic route

diazomethane (186581-53-3, 908094-01-9) + cis/trans-communic acid (2761-77-5) → methyl communate ester (1235-39-8)

Conditions	Yield
In diethyl ether at 0℃; for 1h;	96%
In diethyl ether

cis/trans-communic acid (2761-77-5) → Labda-8(14),12ξ-dien-19-saeure-methylester (10267-06-8, 10267-37-5, 148153-36-0, 148153-37-1)

Conditions	Yield
Multi-step reaction with 2 steps 2: H2 / Pd-C / ethanol View Scheme

cis/trans-communic acid (2761-77-5) → labda-8(17),13E-dien-19-ol (10380-71-9)

Conditions	Yield
Multi-step reaction with 3 steps 2: LiAlH4 / diethyl ether / Heating 3: Na, nPrOH View Scheme
Multi-step reaction with 3 steps 2: Na, EtOH 3: LiAlH4 / diethyl ether / Heating View Scheme

cis/trans-communic acid (2761-77-5) → trans-communol (1156-07-6)

Conditions	Yield
Multi-step reaction with 2 steps 2: LiAlH4 / diethyl ether / Heating View Scheme

cis/trans-communic acid (2761-77-5) → labda-8(17),13E-dien-19-oato de metilo (10267-39-7)

Conditions	Yield
Multi-step reaction with 2 steps 2: Na, EtOH View Scheme

cis/trans-communic acid (2761-77-5) → 13,14,15,16,17-pentanorlabdane-8β,12,19-triol (84105-10-2)

Conditions	Yield
Multi-step reaction with 4 steps 2: H2 / Pd-C / ethanol 3: (i) O3, CHCl3, (ii) H2O 4: LiAlH4 / diethyl ether View Scheme
Multi-step reaction with 3 steps 2: (i) O3, CH2Cl2, (ii) H2O 3: LiAlH4 / diethyl ether View Scheme

cis/trans-communic acid (2761-77-5) → 2-((1R,4aR,5S,8aS)-5-(methoxycarbonyl)-5,8a-dimethyl-2-oxodecahydronaphthalen-1-yl)acetic acid (39668-89-8)

Conditions	Yield
Multi-step reaction with 3 steps 2: H2 / Pd-C / ethanol 3: (i) O3, CHCl3, (ii) H2O View Scheme
Multi-step reaction with 2 steps 2: (i) O3, CH2Cl2, (ii) H2O View Scheme

cis/trans-communic acid (2761-77-5) → dimethyl 8-oxo-13,14,15,16,17-pentanorlabdane-12,19-dioate (81800-51-3)

Conditions	Yield
Multi-step reaction with 4 steps 2: H2 / Pd-C / ethanol 3: (i) O3, CHCl3, (ii) H2O View Scheme
Multi-step reaction with 3 steps 2: (i) O3, CH2Cl2, (ii) H2O View Scheme

Downstream Products

• 15798-13-7 (E)-methyl communate 
• 1235-39-8 cis-communic acid 
• 10178-35-5 methyl ester of cis-communic acid 
• 1235-39-8 methyl communate ester 
• 55306-06-4 13,14,15,16-tetranorlabd-6-ene-12,8β-olide-19-oic acid 
• 55306-07-5 acrostalic acid 
• 426219-82-1 (3aS,5aR,10S,10aR,10bS,10cR)-3a,10b-Dimethyl-10-phenylselanyl-1,2,3,3a,5a,7,10,10a,10b,10c-decahydro-5,8-dioxa-acephenanthrylene-4,9-dione 
• 1156-07-6 cis-communol 
• 1156-07-6 Communol