5α-Hydroxylaxogenin

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5α-Hydroxylaxogenin
Identifiers
  • (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
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC27H42O5
Molar mass446.628 g·mol−1
3D model (JSmol)
  • 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=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, found in the Chinese medicinal plant Smilax sieboldii.[1] It acts as a partial agonist at androgen receptors and has been sold as a bodybuilding supplement and pre-workout product.[2][3]

See also[edit]

References[edit]

  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.
  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.
  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.