LIPID MAPS

Structure Database (LMSD)

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Common Name

4,4-dimethylcholesta-8,14,24-trienol

Systematic Name

4,4-dimethyl-5α-cholesta-8,14,24-trien-3β-ol

Synonyms

4,4-dimethylcholesta-8,11,24-trien-3beta-ol
FF-MAS
Follicular fluid meiosis-activating sterol

LM ID

LMST01010149

Formula

C₂₉H₄₆O

Exact Mass

Calculate m/z

410.354865

Sum Composition

ST 29:3;O

Status

Curated

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Classification

Biological Context

Follicular fluid meiosis-activating sterol (FF-MAS) is an intermediate in cholesterol biosynthesis from lanosterol that is found at high concentrations in mammalian ovarian follicular fluid.¹ It increases survival of human oocytes isolated from patients with polycystic ovarian syndrome (PCOS) and improves cytoplasmic maturation of immature rodent and porcine oocytes in vitro.² FF-MAS promotes completion of meiotic maturation to metaphase II and increases the rate of successful in vitro fertilization (IVF) in isolated mouse oocytes.³ Formulations containing FF-MAS have been used to improve embryo quality and implantation rate during IVF.

This information has been provided by Cayman Chemical

References

1. Bergh, C., Loft, A., Lundin, K., et al. Chromosomal abnormality rate in human pre-embryos derived from in vitro fertilization cycles cultured in the presence of Follicular-Fluid Meiosis Activating Sterol (FF-MAS). Hum. Reprod. 19(9), 2109-2117 (2004).

2. Faerge, I., Strejcek, F., Laurincik, J., et al. The effect of FF-MAS on porcine cumulus-oocyte complex maturation, fertilization and pronucleus formation in vitro. Zygote 14(3), 189-199 (2006).

3. Marín Bivens, C.L., Lindenthal, B., O'Brien, M.J., et al. A synthetic analogue of meiosis-activating sterol (FF-MAS) is a potent agonist promoting meiotic maturation and preimplantation development of mouse oocytes maturing in vitro. Hum. Repod. 19(10), 2340-2344 (2004).

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References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Saccharomyces cerevisiae (#4932)

Saccharomycetes (#4891)

Interactions of the ergosterol biosynthetic pathway with other lipid pathways.,
Biochem Soc Trans, 2005

Pubmed ID: 16246076

Rattus norvegicus (#10116)

Mammalia (#40674)

Sterol 14-demethylase P450 activity expressed in rat gonads: contribution to the formation of mammalian meiosis-activating sterol.,
Biochem Biophys Res Commun, 1996

Pubmed ID: 8687430

String Representations

InChiKey (Click to copy)

LFQXEZVYNCBVDO-PBJLWWPKSA-N

InChi (Click to copy)

InChI=1S/C29H46O/c1-19(2)9-8-10-20(3)22-12-13-23-21-11-14-25-27(4,5)26(30)16-18-29(25,7)24(21)15-17-28(22,23)6/h9,13,20,22,25-26,30H,8,10-12,14-18H2,1-7H3/t20-,22-,25+,26+,28-,29-/m1/s1

SMILES (Click to copy)

C12CC[C@@]3([H])C(C)(C)[C@@H](O)CC[C@]3(C)C=1CC[C@]1(C)[C@@]([H])([C@@](C)([H])CC/C=C(\C)/C)CC=C21