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64284-64-6
Catalog No.:AA00EF9R

64284-64-6 | (3R,5S,10S,13S,17S)-4,4,10,13-tetramethyl-17-[(2R)-6-methylhept-5-en-2-yl]-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-ol

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1mg
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$1,268.00   $887.00
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  • Technical Information
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  • Technical Information
  • Properties
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Technical Information
Catalog Number:
AA00EF9R
Chemical Name:
(3R,5S,10S,13S,17S)-4,4,10,13-tetramethyl-17-[(2R)-6-methylhept-5-en-2-yl]-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-ol
CAS Number:
64284-64-6
Molecular Formula:
C29H46O
Molecular Weight:
410.6749
SMILES:
CC(=CCC[C@H]([C@H]1CC=C2[C@]1(C)CCC1=C2CC[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)C)C
Properties
Properties
 
Form:
Solid  
MP:
120 - 122°C  
Storage:
-20 ℃;  

Computed Properties
 
Complexity:
776  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
6  
Heavy Atom Count:
30  
Hydrogen Bond Acceptor Count:
1  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
4  
XLogP3:
7.8  

Literature

Title: Autoregulation of cholesterol synthesis: physiologic and pathophysiologic consequences.

Journal: Steroids 20110201

Title: Gonadotropin-regulated expressions of lanosterol 14alpha-demethylase, sterol Delta14-reductase and C-4 sterol methyl oxidase contribute to the accumulation of meiosis-activating sterol in rabbit gonads.

Journal: Prostaglandins & other lipid mediators 20100601

Title: Oocyte maturation. Basic and clinical aspects of in vitro maturation (IVM) with special emphasis of the role of FF-MAS.

Journal: Danish medical bulletin 20080201

Title: Are steroids dispensable for meiotic resumption in mammals?

Journal: Trends in endocrinology and metabolism: TEM 20071001

Title: Influence of follicular fluid meiosis-activating sterol on aneuploidy rate and precocious chromatid segregation in aged mouse oocytes.

Journal: Human reproduction (Oxford, England) 20070301

Title: Effect of rescuing donated immature human oocytes derived after FSH/hCG stimulation following in vitro culture with or without Follicular Fluid Meiosis Activating Sterol (FF-MAS)--an embryo chromosomal and morphological analysis.

Journal: Journal of assisted reproduction and genetics 20070301

Title: The effect of FF-MAS on porcine cumulus-oocyte complex maturation, fertilization and pronucleus formation in vitro.

Journal: Zygote (Cambridge, England) 20060801

Title: Meiosis activating sterol (MAS) regulate FSH-induced meiotic resumption of cumulus cell-enclosed porcine oocytes via PKC pathway.

Journal: Molecular and cellular endocrinology 20060425

Title: Follicular sterol composition in gonadotrophin stimulated women with polycystic ovarian syndrome.

Journal: Molecular and cellular endocrinology 20060425

Title: cDNA cloning, genomic structure and expression analysis of the bovine lanosterol 14alpha-demethylase (CYP51) in gonads.

Journal: Biological & pharmaceutical bulletin 20060301

Title: Impact of follicular-fluid meiosis-activating sterol in an albumin-based formulation on the incidence of human pre-embryos with chromosome abnormalities.

Journal: Fertility and sterility 20051001

Title: Meiosis-activating sterol synthesis in rat preovulatory follicle: is it involved in resumption of meiosis?

Journal: Biology of reproduction 20041201

Title: Mouse oocyte meiotic resumption and polar body extrusion in vitro are differentially influenced by FSH, epidermal growth factor and meiosis-activating sterol.

Journal: Human reproduction (Oxford, England) 20041201

Title: Development and validation of a method for the purity determination of (3beta,20R)-4,4-dimethylcholesta-8,14,24-trien-3-ol(FF-MAS) in pharmaceutical products containing recombinant human albumin.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20041025

Title: 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.

Journal: Human reproduction (Oxford, England) 20041001

Title: 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).

Journal: Human reproduction (Oxford, England) 20040901

Title: Phosphatidylinositol 3-kinase and Akt participate in the FSH-induced meiotic maturation of mouse oocytes.

Journal: Molecular reproduction and development 20040901

Title: Quantitation of lanosterol and its major metabolite FF-MAS in an inhibition assay of CYP51 by azoles with atmospheric pressure photoionization based LC-MS/MS.

Journal: Journal of the American Society for Mass Spectrometry 20040801

Title: Action of hypoxanthine and meiosis-activating sterol on oocyte maturation in the mouse is strain specific.

Journal: Reproductive biomedicine online 20040601

Title: A randomized, double-blind, controlled trial of the effect of adding follicular fluid meiosis activating sterol in an ethanol formulation to donated human cumulus-enclosed oocytes before fertilization.

Journal: Fertility and sterility 20040101

Title: Meiosis-activating sterol protects oocytes from precocious chromosome segregation.

Journal: Human reproduction (Oxford, England) 20030901

Title: Two syntheses of FF-MAS.

Journal: Organic letters 20030529

Title: Physiology of meiosis-activating sterol: endogenous formation and mode of action.

Journal: Human reproduction (Oxford, England) 20030101

Title: Progesterone and 17 alpha-OH-progesterone in concentrations similar to that of preovulatory follicular fluid is without effect on resumption of meiosis in mouse cumulus enclosed oocytes cultured in the presence of hypoxanthine.

Journal: Steroids 20021101

Title: Meiosis activating sterols derived from diosgenin.

Journal: Bioorganic & medicinal chemistry letters 20020225

Title: Lanosterol 14alpha-demethylase and MAS sterols in mammalian gametogenesis.

Journal: Molecular and cellular endocrinology 20020222

Title: Role of meiosis activating sterols, MAS, in induced oocyte maturation.

Journal: Molecular and cellular endocrinology 20020222

Title: Is meiosis activating sterol (MAS) an obligatory mediator of meiotic resumption in mammals.

Journal: Molecular and cellular endocrinology 20020222

Title: FF-MAS and its role in mammalian oocyte maturation.

Journal: Ernst Schering Research Foundation workshop 20020101

Title: Gonadotropin-induced accumulation of 4,4-dimethylsterols in mouse ovaries and its temporal relation to meiosis.

Journal: Biology of reproduction 20011201

Title: Resumption of meiosis induced by meiosis-activating sterol has a different signal transduction pathway than spontaneous resumption of meiosis in denuded mouse oocytes cultured in vitro.

Journal: Biology of reproduction 20011201

Title: Relation between the molecular electrostatic potential and activity of some FF-MAS related sterol compounds.

Journal: Bioorganic & medicinal chemistry 20011001

Title: Content of meiosis activating sterols in equine follicular fluids: correlation to follicular size and dominance.

Journal: Theriogenology 20010701

Title: The effects of meiosis activating sterol on in-vitro maturation and fertilization of human oocytes from stimulated and unstimulated ovaries.

Journal: Human reproduction (Oxford, England) 20010301

Title: Activation of meiotic maturation in rat oocytes after treatment with follicular fluid meiosis-activating sterol in vitro and ex vivo.

Journal: Biology of reproduction 20010201

Title: Autoradiographic localization of specific binding of meiosis-activating sterol to cumulus-oocyte complexes from marmoset, cow, and mouse.

Journal: Biology of reproduction 20010201

Title: Meiosis-activating sterol and the maturation of isolated mouse oocytes.

Journal: Biology of reproduction 20010101

Title: Meiosis-activating sterol promotes resumption of meiosis in mouse oocytes cultured in vitro in contrast to related oxysterols.

Journal: Biology of reproduction 19980501

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SDS
Tags:64284-64-6 Molecular Formula|64284-64-6 MDL|64284-64-6 SMILES|64284-64-6 (3R,5S,10S,13S,17S)-4,4,10,13-tetramethyl-17-[(2R)-6-methylhept-5-en-2-yl]-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-ol