2359-73-1

Basic information

• Product Name: (-)-15-Beyerene
• Synonyms: (-)-Beyer-15-ene;(5α,8S,9α,10β,13R)-13-Methyl-17-norkaur-15-ene;(5α,9α,10β)-13-Methyl-17-norkaur-15-ene
• CAS NO: 2359-73-1
• Molecular Formula: C20H32
• Molecular Weight: 272.46808
• Mol File: 2359-73-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 338.3±9.0 °C(Predicted)
• Appearance: /
• Density: 0.97±0.1 g/cm3(Predicted)
• CAS DataBase Reference: (-)-15-Beyerene(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-15-Beyerene(2359-73-1)
• EPA Substance Registry System: (-)-15-Beyerene(2359-73-1)

Safety Data

• Hazardous Substances Data: 2359-73-1(Hazardous Substances Data)

Usage

General Description

(-)-15-Beyerene is a chemical compound found in certain plant species, particularly in the essential oils of juniper and cypress trees. It is a sesquiterpene hydrocarbon with a distinct aroma that is often described as woody and spicy. (-)-15-Beyerene has been studied for its potential medicinal properties, including its anti-inflammatory and anti-cancer effects. It has also been investigated for its antimicrobial activity and potential as a natural insecticide. Overall, (-)-15-Beyerene is a compound with a wide range of potential applications in the fields of medicine, agriculture, and natural products research.

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Relevant articles and documents

Reductive Radical Annulation Strategy toward Bicyclo[3.2.1]octanes: Synthesis of ent-Kaurane and Beyerane Diterpenoids

Here we report a general [3 + 2] radical annulation that allows the facile construction of bicyclo[3.2.1]octane motifs in ent-kaurane- and beyerane-type diterpenoids. This radical annulation is difficult to control but was realized by harnessing an unprecedented and counterintuitive effect of TEMPO. Eleven natural products with a wide array of oxidation states are easily prepared, demonstrating the powerful utility of this straightforward synthetic strategy.

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.