5α-Hydroxylaxogenin

5α-Hydroxylaxogenin
Identifiers
	IUPAC name (1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S,18R)-16,18-dihydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-19-one;
CAS Number	56786-63-1;
PubChem CID	69906537;
ChemSpider	35228242;
UNII	844KE20WT5;
Chemical and physical data
Formula	C27H42O5
Molar mass	446.628 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@@H]1CC[C@@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC(=O)[C@@]6([C@@]5(CC[C@@H](C6)O)C)O)C)C)OC1;
	InChI InChI=1S/C27H42O5/c1-15-5-10-27(31-14-15)16(2)23-21(32-27)12-20-18-11-22(29)26(30)13-17(28)6-9-25(26,4)19(18)7-8-24(20,23)3/h15-21,23,28,30H,5-14H2,1-4H3/t15-,16+,17+,18-,19+,20+,21+,23+,24+,25-,26+,27-/m1/s1; Key:HCRGPOQBVFMZFY-PPCFKNSFSA-N;

5α-Hydroxylaxogenin is a chemical compound which is a semi-synthetic derivative of laxogenin. It is not found in the Chinese medicinal plant Smilax sieboldii, instead, identification of several synthetic impurities by Dr. Chittiboyina's group suggested that it is synthesized from diosgenin.^[1]^[2] It acts as a partial agonist at androgen receptors and has been sold as a bodybuilding supplement and pre-workout product.^[3]

References

^ Tian LW, Zhang Z, Long HL, Zhang YJ (August 2017). "Steroidal Saponins from the Genus Smilax and Their Biological Activities". Natural Products and Bioprospecting. 7 (4): 283–298. doi:10.1007/s13659-017-0139-5. PMC 5507813. PMID 28646341.
^ Avula B, Chittiboyina AG, Bae JY, Haider S, Wang YH, Wang M, et al. (April 2019). "The power of hyphenated chromatography-Time of flight mass spectrometry for unequivocal identification of spirostanes in bodybuilding dietary supplements". Journal of Pharmaceutical and Biomedical Analysis. 167: 74–82. doi:10.1016/j.jpba.2018.12.045. PMID 30753977. S2CID 73429827.
^ Beer C, Keiler AM (July 2022). "Androgenic properties of the dietary supplement 5α-hydroxy-laxogenin". Archives of Toxicology. 96 (7): 2139–2142. doi:10.1007/s00204-022-03283-5. PMC 9151512. PMID 35344071.

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[pmid28646341-1] Tian LW, Zhang Z, Long HL, Zhang YJ (August 2017). "Steroidal Saponins from the Genus Smilax and Their Biological Activities". Natural Products and Bioprospecting. 7 (4): 283–298. doi:10.1007/s13659-017-0139-5. PMC 5507813. PMID 28646341.

[pmid30753977-2] Avula B, Chittiboyina AG, Bae JY, Haider S, Wang YH, Wang M, et al. (April 2019). "The power of hyphenated chromatography-Time of flight mass spectrometry for unequivocal identification of spirostanes in bodybuilding dietary supplements". Journal of Pharmaceutical and Biomedical Analysis. 167: 74–82. doi:10.1016/j.jpba.2018.12.045. PMID 30753977. S2CID 73429827.

[pmid35344071-3] Beer C, Keiler AM (July 2022). "Androgenic properties of the dietary supplement 5α-hydroxy-laxogenin". Archives of Toxicology. 96 (7): 2139–2142. doi:10.1007/s00204-022-03283-5. PMC 9151512. PMID 35344071.

[1]

[2]

[3]

See also

References