21738-16-9

Basic information

• Product Name: Γ8(14)-Sandaracopimaradiene
• Synonyms: (+)-Sandaracopimaradiene;(5β,9β,10α,13S)-Pimara-8(14),15-diene;[4aR,(+)]-1,2,3,4,4a,4bβ,5,6,7,9,10,10aβ-Dodecahydro-1,1,4aα,7-tetramethyl-7β-vinylphenanthrene;ent-Sandaracopimaradiene;Γ8(14)-Sandaracopimaradiene
• CAS NO: 21738-16-9
• Molecular Formula: C₂₀H₃₂
• Molecular Weight: 272.46808
• Mol File: 21738-16-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 337°C at 760 mmHg
• Flash Point: 150.5°C
• Appearance: /
• Density: 0.93g/cm³
• Vapor Pressure: 0.000211mmHg at 25°C
• Refractive Index: 1.514
• CAS DataBase Reference: Γ8(14)-Sandaracopimaradiene(CAS DataBase Reference)
• NIST Chemistry Reference: Γ8(14)-Sandaracopimaradiene(21738-16-9)
• EPA Substance Registry System: Γ8(14)-Sandaracopimaradiene(21738-16-9)

Safety Data

• Hazardous Substances Data: 21738-16-9(Hazardous Substances Data)

Usage

General Description

Γ8(14)-Sandaracopimaradiene is a chemical compound belonging to the class of diterpenoids, which are natural products found in plants. It is derived from sandaracopimaric acid and has been identified in the essential oils of various plant species. Γ8(14)-Sandaracopimaradiene has been studied for its potential biological activities, including antimicrobial and anti-inflammatory properties. It is also being investigated for its potential use in pharmaceutical and agricultural applications. Further research is needed to fully understand the potential benefits and applications of Γ8(14)-Sandaracopimaradiene.

InChI:InChI=1/C20H32/c1-6-19(4)13-10-16-15(14-19)8-9-17-18(2,3)11-7-12-20(16,17)5/h6,14,16-17H,1,7-13H2,2-5H3/t16-,17-,19-,20+/m0/s1

Upstream product

• 6699-20-3 (E,E,E)-geranylgeranyl diphosphate 
• 19380-47-3 (5S,9S,10S)-copalyl diphosphate 
• 142699-00-1 Methanesulfonic acid (1R,4aR,4bS,7R,10aR)-1,4a,7-trimethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-phenanthren-1-ylmethyl ester 
• 24563-84-6 sandaracopimara-8⁽¹⁴⁾,15-dien-18-ol 
• 1686-54-0 methyl sandaracopimarate 
• 142699-02-3 (1R,4aR,4bS,7R,10aR)-1,4a,7-Trimethyl-1-phenylsulfanylmethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-phenanthrene 

Downstream Products

• 24563-84-6 sandaracopimara-8⁽¹⁴⁾,15-dien-18-ol 
• 6697-24-1 isopimara-8,15-diene 

Relevant articles and documents

Probing Labdane-Related Diterpenoid Biosynthesis in the Fungal Genus Aspergillus

While terpenoid production is generally associated with plants, a variety of fungi contain operons predicted to lead to such biosynthesis. Notably, fungi contain a number of cyclases characteristic of labdane-related diterpenoid metabolism, which have not been much explored. These also are often found near cytochrome P450 (CYP) mono-oxygenases that presumably further decorate the ensuing diterpene, suggesting that these fungi might produce more elaborate diterpenoids. To probe the functional diversity of such biosynthetic capacity, an investigation of the phylogenetically diverse cyclases and associated CYPs from the fungal genus Aspergillus was undertaken, revealing their ability to produce isopimaradiene-derived diterpenoids. Intriguingly, labdane-related diterpenoid biosynthetic genes are largely found in plant-associated fungi, hinting that these natural products may play a role in such interactions. Accordingly, it is hypothesized here that isopimarane production may assist the plant-saprophytic lifestyle of Aspergillus fungi.

Partial Synthesis of 9,10-Syn Diterpenes via Tosylhydrazone Reduction: (-)-(9β)-Pimara-7,15-diene and (-)-(9β)-Isopimaradiene

(9β)-Pimara-7,15-diene (3), a proposed intermediate in the biosynthesis of the momilactone phytoalexins (1 and 2) from rice, and its C-13 epimer, (9β)-isopimara-7,15-diene (4), were synthesized from methyl pimara- and isopimara-8,15-dien-18-oates (8b and 8a, respectively).Allylic oxidation of 8a and 8b as well as the derived diterpene hydrocarbons 15a and 15b with chromium trioxide-dipyridine complex afforded 8,15-dien-7-ones 9a, 9b, 16a, and 16b (35-54percent).Lithium-ammonia reduction of 9a, 16a, and 16b gave predominantly trans,anti,trans-isopimara- and -pimara-15-en-7-ones 10, 17a, and 17b.In contrast, catecholborane reduction of the tosylhydrazones of 9a and 9b provided methyl (9β)-isopimara- and (9β)-pimara-7,15-dien-20-oates (23a and 23b) having the 9,10-syn stereochemistry.The parent diterpenes, 3 and 4, were obtained by carboxyl-to-methyl conversions.In a collaborative investigation 3 was tentatively identified as one of five diterpene hydrocarbons produced upon incubation of (E,E,E)-geranylgeranyl pyrophosphate with a crude enzyme extract from UV-treated rice plants.