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08172

Sigma-Aldrich

Cycloartenol

≥90% (GC)

Synonym(s):

(3S,5R,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hex-4-enyl)-4,4,13,14-tetramethyl-tetradecahydro-cyclopropa[9,10]cyclopenta[a]phenanthren-3-ol, 9,19-Cyclo-24-lanosten-3β-ol, Handianol

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About This Item

Empirical Formula (Hill Notation):
C30H50O
CAS Number:
469-38-5
Molecular Weight:
426.72
Beilstein:
2224850
UNSPSC Code:
12352211
NACRES:
NA.77

Assay

≥90% (GC)

form

powder

InChI

1S/C30H50O/c1-20(2)9-8-10-21(3)22-13-15-28(7)24-12-11-23-26(4,5)25(31)14-16-29(23)19-30(24,29)18-17-27(22,28)6/h9,21-25,31H,8,10-19H2,1-7H3/t21-,22-,23+,24+,25+,27-,28+,29-,30+/m1/s1

InChI key

ONQRKEUAIJMULO-YBXTVTTCSA-N

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Application

  • Genome-Wide Investigation of Oxidosqualene Cyclase Genes Deciphers the Genetic Basis of Triterpene Biosynthesis in Tea Plants - Research on cycloartenol′s synthesis pathways through the genetic study of oxidosqualene cyclase in tea plants, providing insights into the enhancement of plant sterols beneficial for human health (Du et al., 2024).

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Anita Loeschcke et al.
PloS one, 12(12), e0189816-e0189816 (2017-12-28)
Cyclic triterpenes constitute one of the most diverse groups of plant natural products. Besides the intriguing biochemistry of their biosynthetic pathways, plant triterpenes exhibit versatile bioactivities, including antimicrobial effects against plant and human pathogens. While prokaryotes have been extensively used
Go Atsumi et al.
Scientific reports, 8(1), 14804-14804 (2018-10-06)
Secondary metabolites in plants play important roles in defence against biotic and abiotic stresses. Although the biosynthesis pathways of secondary metabolites have been extensively studied, the regulatory mechanism of gene expression involved in these pathways remains poorly understood. In this
Kiyoshi Ohyama et al.
Proceedings of the National Academy of Sciences of the United States of America, 106(3), 725-730 (2009-01-14)
The differences between the biosynthesis of sterols in higher plants and yeast/mammals are believed to originate at the cyclization step of oxidosqualene, which is cyclized to cycloartenol in higher plants and lanosterol in yeast/mammals. Recently, lanosterol synthase genes were identified
Laurent F Wentzinger et al.
Plant physiology, 130(1), 334-346 (2002-09-13)
To get some insight into the regulatory mechanisms controlling the sterol branch of the mevalonate pathway, tobacco (Nicotiana tabacum cv Bright Yellow-2) cell suspensions were treated with squalestatin-1 and terbinafine, two specific inhibitors of squalene synthase (SQS) and squalene epoxidase
X Qi et al.
Proceedings of the National Academy of Sciences of the United States of America, 101(21), 8233-8238 (2004-05-19)
The evolution of the ability to synthesize specialized metabolites is likely to have been key for survival and diversification of different plant species. Oats (Avena spp.) produce antimicrobial triterpenoids (avenacins) that protect against disease. The oat beta-amyrin synthase gene AsbAS1
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