469-86-3

Basic information

• Product Name: [5α,9α,10β,(+)]-Kaur-16-ene
• Synonyms: [5α,8α,9α,10β,13α,(+)]-Kaur-16-ene;[5α,9α,10β,(+)]-Kaur-16-ene;Sciadopiten
• CAS NO: 469-86-3
• Molecular Formula: C₂₀H₃₂
• Molecular Weight: 272.46808
• Mol File: 469-86-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 95-96 °C
• Boiling Point: 130-135 °C(Press: 0.3 Torr)
• Appearance: /
• Density: 0.97±0.1 g/cm3(Predicted)
• CAS DataBase Reference: [5α,9α,10β,(+)]-Kaur-16-ene(CAS DataBase Reference)
• NIST Chemistry Reference: [5α,9α,10β,(+)]-Kaur-16-ene(469-86-3)
• EPA Substance Registry System: [5α,9α,10β,(+)]-Kaur-16-ene(469-86-3)

Safety Data

• Hazardous Substances Data: 469-86-3(Hazardous Substances Data)

Usage

Description

[5α,9α,10β,(+)]-Kaur-16-ene is a naturally occurring diterpene compound found in various plant species, including pine trees. It belongs to the kaurane family of compounds, which are recognized for their diverse biological activities such as anti-inflammatory, anti-cancer, and antimicrobial properties. This specific compound has garnered research interest due to its potential in the development of new pharmaceuticals and natural products, making it a promising candidate for further study and applications in medicine and agriculture.

Uses

Used in Pharmaceutical Applications:
[5α,9α,10β,(+)]-Kaur-16-ene is used as a potential pharmaceutical agent for its anti-inflammatory, anti-cancer, and antimicrobial properties. Its unique structure and biological activities contribute to its potential in the development of new drugs and natural products, particularly in the fields of medicine and agriculture.
Used in Agricultural Applications:
In agriculture, [5α,9α,10β,(+)]-Kaur-16-ene is used as a natural compound with potential antimicrobial properties. Its ability to combat various pathogens makes it a promising candidate for the development of new, eco-friendly, and sustainable solutions to protect crops and enhance agricultural productivity.

Upstream product

• 511-85-3 isophyllocladene 
• 21561-90-0 C₂₀H₃₆O₇P₂ 
• 28235-66-7 ent-15-Kauren-6α,20-diol 
• 90457-97-9 ent-kauran-17-ol 
• 112609-07-1 ent-17-iodokaurane 
• 150-97-0 D,L-mevalonic acid 
• 36146-33-5 ent-15-Kauren-6-on-20-al 

Downstream Products

• 483-87-4 1,7-dimethylphenanthrene 
• 483-65-8 Retene 
• 4733-53-3 (+)-β-Dihydrophyllocladen 
• 10179-10-9 Phyllocladen-16-ol-15α 
• 40140-48-5 C₂₆H₃₈N₂O₂S 
• 27898-45-9 phylloclaedan-16β-yl 3,5-dinitrobenzoate 
• 4608-45-1 C₂₀H₃₁Br 
• 4627-79-6 C₂₀H₃₂O 
• 4627-79-6 Phylloclad-15-en-17-ol 
• 43084-79-3 17-Benzoyloxy-phyllocladen-⁽¹⁵⁾ 
• 16836-31-0 16α,17-ent-kauranediol 
• 14696-33-4 ent-kaur-15-en-17-ol 
• 2359-73-1 (+)-hibaene 
• 43084-80-6 C₂₇H₃₆O₂ 

Relevant articles and documents

Functional characterization of wheat ent-kaurene(-like) synthases indicates continuing evolution of labdane-related diterpenoid metabolism in the cereals

Wheat (Triticum aestivum) and rice (Oryza sativa) are two of the most agriculturally important cereal crop plants. Rice is known to produce numerous diterpenoid natural products that serve as phytoalexins and/or allelochemicals. Specifically, these are labdane-related diterpenoids, derived from a characteristic labdadienyl/copalyl diphosphate (CPP), whose biosynthetic relationship to gibberellin biosynthesis is evident from the relevant expanded and functionally diverse family of ent-kaurene synthase-like (KSL) genes found in rice the (OsKSLs). Herein reported is the biochemical characterization of a similarly expansive family of KSL from wheat (the TaKSLs). In particular, beyond ent-kaurene synthases (KS), wheat also contains several biochemically diversified KSLs. These react either with the ent-CPP intermediate common to gibberellin biosynthesis or with the normal stereoisomer of CPP that also is found in wheat (as demonstrated by the accompanying paper describing the wheat CPP synthases). Comparison with a barley (Hordeum vulgare) KS indicates conservation of monocot KS, with early and continued expansion and functional diversification of KSLs in at least the small grain cereals. In addition, some of the TaKSLs that utilize normal CPP also will react with syn-CPP, echoing previous findings with the OsKSL family, with such enzymatic promiscuity/elasticity providing insight into the continuing evolution of diterpenoid metabolism in the cereal crop plant family, as well as more generally, which is discussed here.

SUPERACID ISOMERIZATION OF PHYLLOCLADENE, ISOPHYLLOCLADENE, AND PHYLLOCLADANOL

It has been established that, on interaction with a superacid, phyllocladene (XI), isophyllocladene (XV), and phyllocladan-16-ol (XIX) give identical mixtures of substances which include phyllocladene (XI), isophyllocladene (XV), neoisoatisene (XX), tetracyclic hydrocarbons with a new carbon skeleton (XXI) and (XXII), and a mixture of methyl ethers of alcohols formed as the result of the addition of methanol to the carbocations arising on the protonation of the above-mentioned hydrocarbons.

BIOSYNTHESIS OF GIBBERELLIN A12-ALDEHYDE, GIBBERELLIN A12 AND THEIR KAURENOID PRECURSORS FROM MEVALONIC ACID IN A CELL-FREE SYSTEM FROM IMMATURE SEED OF PHASEOLUS COCCINEUS

A cell-free system capable of gibberellin (GA) biosynthesis has been prepared from immature seed of Phaseolus coccineus.This system converted mevalonic acid (MVA) to ent-kaurene, ent-kaurenoic acid, ent-kauradienoic acid, ent-7α-hydroxykaurenoic acid, ent-6α,7α-dihydroxykaurenoic acid, GA12-aldehyde and GA12. ent-Kaurene was converted to ent-kaurenol, ent-kaurenal, ent-kaurenoic acid and ent-7α-hydroxykaurenoic acid.All identifications were by GC/MC.The pathway from MVA to GA12-aldehyde in this species thus appears to be the same as that found in cell-free preparations derived from immature seed of other species.Key Word Index-Phaseolus coccineus; Leguminosae; runner bean; seed development; biosynthesis; cell-free system; HPLC; GC/MC; gibberellin.