1686-61-9 Usage
Chemical class
Diterpenoids These are a group of naturally occurring organic compounds that are derived from the diterpene class of terpenoids.
Molecular structure
Complex arrangement of carbon and hydrogen atoms The compound has a unique and intricate arrangement of these atoms, which contributes to its biological activities.
Presence of functional groups
Vinyl group and norabietane skeleton The vinyl group is a carbon-carbon double bond, while the norabietane skeleton is a specific carbon framework found in this compound.
Natural occurrence
Commonly found in plants 13-Vinyl-16,17-dinorabieta-8(14)-ene has been isolated from various plant sources in nature.
Biological activities
Exhibits potential antimicrobial, antifungal, and anti-inflammatory effects These properties make it a subject of interest for further research and potential applications in medicine and pharmacology.
Research interest
Fields of natural product chemistry, pharmacology, and medicinal chemistry Due to its complex structure and potential biological activities, this compound is of interest to researchers in these areas.
Isolation
Obtained from natural sources The compound is typically isolated from plants through various extraction and purification techniques.
Structural analysis
Requires advanced analytical techniques The complex structure of 13-Vinyl-16,17-dinorabieta-8(14)-ene necessitates the use of advanced analytical methods, such as nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry, for its characterization.
Potential applications
As a lead compound for drug development The compound's pharmacological properties make it a potential candidate for the development of new drugs targeting various diseases and conditions.
Challenges
Complex synthesis and limited availability The complex structure of 13-Vinyl-16,17-dinorabieta-8(14)-ene presents challenges in its synthesis, and its limited availability from natural sources may hinder large-scale research and development efforts.
Check Digit Verification of cas no
The CAS Registry Mumber 1686-61-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,6,8 and 6 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 1686-61:
(6*1)+(5*6)+(4*8)+(3*6)+(2*6)+(1*1)=99
99 % 10 = 9
So 1686-61-9 is a valid CAS Registry Number.
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/h7,9,12,15-16H,6,8,10-11,13-14H2,1-5H3/t15-,16-,19+,20+/m0/s1
1686-61-9Relevant articles and documents
Probing Labdane-Related Diterpenoid Biosynthesis in the Fungal Genus Aspergillus
Xu, Meimei,Hillwig, Matthew L.,Tiernan, Mollie S.,Peters, Reuben J.
, p. 328 - 333 (2017/03/09)
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
Chu, Min,Coates, Robert M.
, p. 4590 - 4597 (2007/10/02)
(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.
