76497-69-3

Basic information

• Product Name: 15,16-Dir-8(17),11-labdadien-13-one
• Synonyms: 15,16-Dir-8(17),11-labdadien-13-one;15,16-Dinor-8(17),11-labdadien-13-one;15,16-Dinorlabda-8(17),11-dien-13-one
• CAS NO: 76497-69-3
• Molecular Formula: C₁₈H₂₈O
• Molecular Weight: 260.41432
• Mol File: 76497-69-3.mol
• Article Data: 1

Chemical Properties

• Melting Point: 146-147 °C
• Boiling Point: 343.9±21.0 °C(Predicted)
• Appearance: /
• Density: 0.94±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 15,16-Dir-8(17),11-labdadien-13-one(CAS DataBase Reference)
• NIST Chemistry Reference: 15,16-Dir-8(17),11-labdadien-13-one(76497-69-3)
• EPA Substance Registry System: 15,16-Dir-8(17),11-labdadien-13-one(76497-69-3)

Safety Data

• Hazardous Substances Data: 76497-69-3(Hazardous Substances Data)

Usage

General Description

15,16-Dir-8(17),11-labdadien-13-one is a chemical compound belonging to the diterpene class of compounds. It is a labdane-type diterpenoid that is found in various plant species and has been isolated from the root of the Rhodiola crenulata plant. It is characterized by its unique chemical structure, containing a 15,16-double bond, an 8(17)-enone group, and a 11-labdadiene skeleton. 15,16-Dir-8(17),11-labdadien-13-one has been studied for its potential biological activities, including its anti-inflammatory, anti-cancer, and neuroprotective properties. Its complex structure and potential medicinal properties make it an interesting subject of research in the field of natural products and medicinal chemistry.

Upstream product

• 76467-03-3 labda-8⁽¹⁷⁾,12-diene 
• 596-85-0 epimanool 
• 40768-86-3 14,15-dihydromanool 

Relevant articles and documents

Photosensitized Oxygenation of Labda-8(17),12-diene, Labda-8(17),13-diene, and the Biformenes. Synthesis of Pumiloxide

Reactions of the title compounds with singlet oxygen were studied.In labda-8(17),12-diene (2; 7:3 mixture of E and Z isomers), syn addition leading to 7 (58percent) was predominant.Smaller amounts of 8 (20percent) by syn addition to (E)-2 or anti addition to (Z)-2, 9 (5percent), 10 (2,5percent), and 11(1.5percent) were also formed. (E)-Labda-8(17),13-diene ((E)-3) gave 29percent 12 and 40percent 13 by syn addition, whereas (Z)-3 gave 57percent 12 by syn addition and 19percent 13 by anti addition.In trans-biformene (5) syn attack at C-12 to give 15 (27percent), 16 (10percent), 18 (12percent), and 19 (4percent) was greatly preferred to syn attack at C-13 to give 17 (6percent).In cis-biformene (6) syn attack at C-13 to give 17 (39percent) predominated slightly over anti attack at C-12 to give 15 (13percent), 16 (8percent), 18 (4percent), and 19 (4percent).Diels-Alder reactions with singlet oxygen leading to epidioxides 20 and 21 were relatively unimportant (7percent from 5, 5percent from 6).The epidioxides were converted to the naturally occurring furanolabdane pumiloxide (22).