Norcycloartenol

Norcycloartenol
Names
	Other names 4α,14α-dimethyl-9β,19-cyclo-5α-cholest-24-en-3β-ol
Identifiers
CAS Number	60485-38-3;
3D model (JSmol)	Interactive image;
ChemSpider	58837777;
PubChem CID	102515312;
	InChI InChI=1S/C29H48O/c1-19(2)8-7-9-20(3)22-12-14-27(6)25-11-10-23-21(4)24(30)13-15-28(23)18-29(25,28)17-16-26(22,27)5/h8,20-25,30H,7,9-18H2,1-6H3/t20-,21+,22-,23+,24+,25+,26-,27+,28?,29?/m1/s1 Key: XZEUYTKSAYNYPK-YETBRXCGSA-N;
	SMILES C[C@H]1[C@@H]2CC[C@H]3[C@@]4(CC[C@@H]([C@]4(CCC35C2(C5)CC[C@@H]1O)C)[C@H](C)CCC=C(C)C)C;
Properties
Chemical formula	C29H48O
Molar mass	412.702 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

29- or 31-Norcycloartenol^{[note 1]}, also called 4α,14α-dimethyl-9β,19-cyclo-5α-cholest-24-en-3β-ol, is a Metabolic intermediate of plant sterol biosynthesis.^[1]^[2]^[3]^[4] In the pathway, it is transformed from demethylation of cycloartenol, then 9,19-cyclopropyl-ring opening reaction occurs to 29-Norlanosterol.^[5]

Note

^ zoology and botany are different in numbering of steroids side chain, 24¹ to 28, 24² to 29

References

^ Zheng, S; Ma, Z; Ye, J; Wang, G; Wang, R; Zhou, H; Zeng, S; Jiang, H (1 January 2014). "Determination of three triterpene alcohols in rat plasma after oral administration of pollen of Brassica campestris based on the utilization of fetal bovine serum as surrogate matrix". Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences. 944: 11–7. doi:10.1016/j.jchromb.2013.10.044. PMID 24291607.
^ Bellamine, A; Mangla, AT; Dennis, AL; Nes, WD; Waterman, MR (January 2001). "Structural requirements for substrate recognition of Mycobacterium tuberculosis 14 alpha-demethylase: implications for sterol biosynthesis". Journal of Lipid Research. 42 (1): 128–36. doi:10.1016/S0022-2275(20)32344-0. PMID 11160374.
^ Bayer, M; Proksch, P; Felsner, I; Brenden, H; Kohne, Z; Walli, R; Duong, TN; Götz, C; Krutmann, J; Grether-Beck, S (November 2011). "Photoprotection against UVAR: effective triterpenoids require a lipid raft stabilizing chemical structure". Experimental Dermatology. 20 (11): 955–8. doi:10.1111/j.1600-0625.2011.01350.x. PMID 21824200. S2CID 28583844.
^ Hartmann, MA; Perret, AM; Carde, JP; Cassagne, C; Moreau, P (8 August 2002). "Inhibition of the sterol pathway in leek seedlings impairs phosphatidylserine and glucosylceramide synthesis but triggers an accumulation of triacylglycerols". Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids. 1583 (3): 285–96. doi:10.1016/s1388-1981(02)00249-4. PMID 12176396.
^ "Rosa chinensis plant sterol biosynthesis II". pmn.plantcyc.org.

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[1] zoology and botany are different in numbering of steroids side chain, 24¹ to 28, 24² to 29

[2] Zheng, S; Ma, Z; Ye, J; Wang, G; Wang, R; Zhou, H; Zeng, S; Jiang, H (1 January 2014). "Determination of three triterpene alcohols in rat plasma after oral administration of pollen of Brassica campestris based on the utilization of fetal bovine serum as surrogate matrix". Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences. 944: 11–7. doi:10.1016/j.jchromb.2013.10.044. PMID 24291607.

[3] Bellamine, A; Mangla, AT; Dennis, AL; Nes, WD; Waterman, MR (January 2001). "Structural requirements for substrate recognition of Mycobacterium tuberculosis 14 alpha-demethylase: implications for sterol biosynthesis". Journal of Lipid Research. 42 (1): 128–36. doi:10.1016/S0022-2275(20)32344-0. PMID 11160374.

[4] Bayer, M; Proksch, P; Felsner, I; Brenden, H; Kohne, Z; Walli, R; Duong, TN; Götz, C; Krutmann, J; Grether-Beck, S (November 2011). "Photoprotection against UVAR: effective triterpenoids require a lipid raft stabilizing chemical structure". Experimental Dermatology. 20 (11): 955–8. doi:10.1111/j.1600-0625.2011.01350.x. PMID 21824200. S2CID 28583844.

[5] Hartmann, MA; Perret, AM; Carde, JP; Cassagne, C; Moreau, P (8 August 2002). "Inhibition of the sterol pathway in leek seedlings impairs phosphatidylserine and glucosylceramide synthesis but triggers an accumulation of triacylglycerols". Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids. 1583 (3): 285–96. doi:10.1016/s1388-1981(02)00249-4. PMID 12176396.

[6] "Rosa chinensis plant sterol biosynthesis II". pmn.plantcyc.org.

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