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80-92-2,MFCD00064141
Catalog No.:AA00344A

80-92-2 | 5β-Pregnane-3α,20α-diol

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5mg
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1 week  
$114.00   $80.00
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10mg
99%
1 week  
$154.00   $108.00
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50mg
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$360.00   $252.00
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100mg
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00344A
Chemical Name:
5β-Pregnane-3α,20α-diol
CAS Number:
80-92-2
Molecular Formula:
C21H36O2
Molecular Weight:
320.5093
MDL Number:
MFCD00064141
SMILES:
O[C@@H]1CC[C@]2([C@@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](O)C)C)C
Properties
Properties
 
Form:
Solid  
MP:
236-239˚C  
Storage:
Room Temperature;  

Computed Properties
 
Complexity:
463  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
9  
Heavy Atom Count:
23  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
1  
XLogP3:
5.2  

Literature

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Journal: American journal of primatology 20121101

Title: Development of a GC/C/IRMS method--confirmation of a novel steroid profiling approach in doping control.

Journal: Steroids 20120901

Title: Progesterone, pregnanediol-3-glucuronide, relaxin and oestrone sulphate concentrations in saliva, milk and urine of female alpacas (Vicugna pacos) and their application in pregnancy diagnosis.

Journal: The Veterinary record 20120825

Title: CYP3A variation, premenopausal estrone levels, and breast cancer risk.

Journal: Journal of the National Cancer Institute 20120502

Title: Hormonal and experiential predictors of infant survivorship and maternal behavior in a monogamous primate (Callicebus cupreus).

Journal: American journal of primatology 20120501

Title: Urinary steroid profile in early pregnancy after in vitro fertilization.

Journal: Acta obstetricia et gynecologica Scandinavica 20120501

Title: Temperament and ovarian reproductive hormones in women: evidence from a study during the entire menstrual cycle.

Journal: Hormones and behavior 20120401

Title: Monitoring of ovarian activity by measurement of urinary excretion rates of estrone glucuronide and pregnanediol glucuronide using the Ovarian Monitor, Part II: reliability of home testing.

Journal: Human reproduction (Oxford, England) 20120201

Title: Hormonal monitoring of reproductive status in monogamous wild female owl monkeys (Aotus azarai) of the Argentinean Chaco.

Journal: Folia primatologica; international journal of primatology 20111201

Title: Estrogen and peptide YY are associated with bone mineral density in premenopausal exercising women.

Journal: Bone 20110801

Title: The effects of a long-term psychosocial stress on reproductive indicators in the baboon.

Journal: American journal of physical anthropology 20110801

Title: Hoodia gordonii: an up-to-date review of a commercially important anti-obesity plant.

Journal: Planta medica 20110701

Title: Systematic comparison of δ13C measurements of testosterone and derivative steroids in a freeze-dried urine candidate reference material for sports drug testing by gas chromatography/combustion/isotope ratio mass spectrometry and uncertainty evaluation using four different metrological approaches.

Journal: Rapid communications in mass spectrometry : RCM 20110615

Title: Synthesis of Hoodigogenin A, aglycone of natural appetite suppressant glycosteroids extracted from Hoodia gordonii.

Journal: Steroids 20110601

Title: Investigations on changes in ¹³C/¹²C ratios of endogenous urinary steroids after pregnenolone administration.

Journal: Drug testing and analysis 20110501

Title: Circulating leptin concentrations do not distinguish menstrual status in exercising women.

Journal: Human reproduction (Oxford, England) 20110301

Title: Effects of early pregnancy loss on hormone levels in the subsequent menstrual cycle.

Journal: Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology 20101201

Title: Estrogen and progesterone exposure is reduced in response to energy deficiency in women aged 25-40 years.

Journal: Human reproduction (Oxford, England) 20100901

Title: [Pregnanediol (P2), pregnanetriol (P3)].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20100701

Title: Characterizing the reproductive hormone milieu in infertile women with diminished ovarian reserve.

Journal: Fertility and sterility 20100301

Title: High prevalence of subtle and severe menstrual disturbances in exercising women: confirmation using daily hormone measures.

Journal: Human reproduction (Oxford, England) 20100201

Title: Characterization of in vitro pharmacokinetic properties of hoodigogenin A from Hoodia gordonii.

Journal: Planta medica 20100101

Title: [Progesterone and pregnanediol-glucuronid concentrations in saliva, milk and urine of female alpacas and their application in pregnancy diagnosis].

Journal: Berliner und Munchener tierarztliche Wochenschrift 20100101

Title: Effects of antenatal corticosteroids on urinary markers of the initiation of lactation in pregnant women.

Journal: Breastfeeding medicine : the official journal of the Academy of Breastfeeding Medicine 20091201

Title: Determination of 13C/12C ratios of urinary epitestosterone and its main metabolites 5alpha- and 5beta-androstane-3alpha, 17alpha-diol.

Journal: Drug testing and analysis 20091101

Title: Partial recovery of luteal function after bariatric surgery in obese women.

Journal: Fertility and sterility 20091001

Title: Detecting evidence of luteal activity by least-squares quantitative basal temperature analysis against urinary progesterone metabolites and the effect of wake-time variability.

Journal: European journal of obstetrics, gynecology, and reproductive biology 20090901

Title: Development of an enzyme immunoassay for urinary pregnanediol-3-glucuronide in a female giant panda (Ailuropoda melanoleuca).

Journal: The Journal of veterinary medical science 20090701

Title: Seasonal profiles of ovarian activity in Iberian lynx (Lynx pardinus) based on urinary hormone metabolite analyses.

Journal: Reproduction in domestic animals = Zuchthygiene 20090701

Title: The effect of the neuroactive steroid 5beta-pregnane-3beta, 20(R)-diol on the time course of GABA evoked currents is different to that of pregnenolone sulphate.

Journal: European journal of pharmacology 20090301

Title: Total and unopposed estrogen exposure across stages of the transition to menopause.

Journal: Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20090301

Title: The effect of exercise and estrogen on osteoprotegerin in premenopausal women.

Journal: Bone 20090101

Title: Growth inhibition and ultrastructural alterations induced by Delta24(25)-sterol methyltransferase inhibitors in Candida spp. isolates, including non-albicans organisms.

Journal: BMC microbiology 20090101

Title: Progesterone and ovulation across stages of the transition to menopause.

Journal: Menopause (New York, N.Y.) 20090101

Title: Effects of the selective progesterone receptor modulator asoprisnil on uterine artery blood flow, ovarian activity, and clinical symptoms in patients with uterine leiomyomata scheduled for hysterectomy.

Journal: The Journal of clinical endocrinology and metabolism 20081201

Title: Facilitated acquisition of the classically conditioned eyeblink response in women taking oral contraceptives.

Journal: Behavioural pharmacology 20081201

Title: Cognitive dietary restraint: impact on bone, menstrual and metabolic status in young women.

Journal: Physiology & behavior 20080903

Title: Progesterone metabolites rapidly stimulate calcium influx in human platelets by a src-dependent pathway.

Journal: Steroids 20080801

Title: C-reactive protein across the menstrual cycle.

Journal: American journal of physical anthropology 20080601

Title: Neurosteroids 3beta, 20 (R/S)-pregnandiols decrease offset rate of the GABA-site activation at the recombinant GABA A receptor.

Journal: European journal of pharmacology 20080531

Title: Factors related to declining luteal function in women during the menopausal transition.

Journal: The Journal of clinical endocrinology and metabolism 20080501

Title: Novel potent and selective bile acid derivatives as TGR5 agonists: biological screening, structure-activity relationships, and molecular modeling studies.

Journal: Journal of medicinal chemistry 20080327

Title: Effects of continuous versus cyclical oral contraception: a randomized controlled trial.

Journal: The Journal of clinical endocrinology and metabolism 20080201

Title: Luteal phase estrogen is decreased in regularly menstruating older women compared with a reference population of younger women.

Journal: Menopause (New York, N.Y.) 20080101

Title: Reproductive and behavioral characteristics of aging in female Asian colobines.

Journal: Interdisciplinary topics in gerontology 20080101

Title: Reproductive life history traits of female orangutans (Pongo spp.).

Journal: Interdisciplinary topics in gerontology 20080101

Title: Relation of daily urinary hormone patterns to vasomotor symptoms in a racially/ethnically diverse sample of midlife women: study of women's health across the nation.

Journal: Reproductive sciences (Thousand Oaks, Calif.) 20071201

Title: Lifestyle and reproductive factors associated with follicular phase length.

Journal: Journal of women's health (2002) 20071101

Title: Characteristics of the urinary luteinizing hormone surge in young ovulatory women.

Journal: Fertility and sterility 20070901

Title: Ovarian steroids and premenstrual symptoms: a comparison of group differences and intra-individual patterns.

Journal: Research in nursing & health 20070601

Title: Long-term estrogen deficiency lowers regional blood flow, resting systolic blood pressure, and heart rate in exercising premenopausal women.

Journal: American journal of physiology. Endocrinology and metabolism 20070501

Title: Characterizing daily urinary hormone profiles for women at midlife using functional data analysis.

Journal: American journal of epidemiology 20070415

Title: Clinical aspects and luteal phase assessment in patients with recurrent vulvovaginal candidiasis.

Journal: European journal of obstetrics, gynecology, and reproductive biology 20070401

Title: Exercise training effects on premenstrual distress and ovarian steroid hormones.

Journal: European journal of applied physiology 20070101

Title: Age-related changes in bone turnover markers and ovarian hormones in premenopausal and postmenopausal Indian women.

Journal: Journal of clinical laboratory analysis 20070101

Title: Neurosteroid modulation of recombinant rat alpha5beta2gamma2L and alpha1beta2gamma2L GABA(A) receptors in Xenopus oocyte.

Journal: European journal of pharmacology 20061010

Title: Comparative endocrine investigations in three bear species based on urinary steroid metabolites and volatiles.

Journal: Theriogenology 20061001

Title: Neuromuscular performance and knee laxity do not change across the menstrual cycle in female athletes.

Journal: Knee surgery, sports traumatology, arthroscopy : official journal of the ESSKA 20060901

Title: Ovulation detection methods for urinary hormones: precision, daily and intermittent sampling and a combined hierarchical method.

Journal: Human reproduction (Oxford, England) 20060601

Title: Relation of cardiovascular risk factors in women approaching menopause to menstrual cycle characteristics and reproductive hormones in the follicular and luteal phases.

Journal: The Journal of clinical endocrinology and metabolism 20060501

Title: Hormone levels before and after tubal sterilization.

Journal: Contraception 20060501

Title: Gonadotropin stimulation of steroid synthesis and metabolism in the Rana pipiens ovarian follicle: sequential changes in endogenous steroids during ovulation, fertilization and cleavage stages.

Journal: The Journal of steroid biochemistry and molecular biology 20060501

Title: Distribution of postpartum amenorrhea in rural Bangladeshi women.

Journal: American journal of physical anthropology 20060401

Title: Menstrual cycle, trait estrogen level, and masculinity preferences in the human voice.

Journal: Hormones and behavior 20060201

Title: Facial appearance is a cue to oestrogen levels in women.

Journal: Proceedings. Biological sciences 20060122

Title: Serum creatine kinase activity varies with ovulatory status in regularly exercising, premenopausal women.

Journal: Hormone research 20060101

Title: Reproductive endocrinology of wild female chimpanzees (Pan troglodytes schweinfurthii): methodological considerations and the role of hormones in sex and conception.

Journal: American journal of primatology 20050901

Title: [Pregnanediol (P2), pregnanetriol (P3)].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20050801

Title: Biological and hormonal markers of chlamydia, human papillomavirus, and bacterial vaginosis among adolescents attending genitourinary medicine clinics.

Journal: Sexually transmitted infections 20050401

Title: Effect of environmental tobacco smoke on levels of urinary hormone markers.

Journal: Environmental health perspectives 20050401

Title: Urinary marker of oral pregnenolone administration.

Journal: Steroids 20050301

Title: Predicting menstrual migraine with a home-use fertility monitor.

Journal: Neurology 20050208

Title: Studies on reproductive endocrinology in non-human primates: application of non-invasive methods.

Journal: The Journal of reproduction and development 20050201

Title: Sequential classification of endocrine stages during reproductive aging in women: the FREEDOM study.

Journal: Menopause (New York, N.Y.) 20050101

Title: Urinary sex steroid excretion levels during a soy intervention among young girls: a pilot study.

Journal: Nutrition and cancer 20050101

Title: Monitoring reproductive aging in a 5-year prospective study: aggregate and individual changes in steroid hormones and menstrual cycle lengths with age.

Journal: Menopause (New York, N.Y.) 20050101

Title: Relationship between ovarian cycle phase and sexual behavior in female Japanese macaques (Macaca fuscata).

Journal: American journal of physical anthropology 20041201

Title: Fecal steroid analysis for monitoring reproduction in the sun bear (Helarctos malayanus).

Journal: Theriogenology 20041201

Title: Hormonal correlates for the initiation of breast-feeding in Bangladeshi women.

Journal: Hormones and behavior 20041101

Title: Origins and consequences of the elongation of the human menstrual cycle during the menopausal transition: the FREEDOM Study.

Journal: The Journal of clinical endocrinology and metabolism 20041001

Title: Caffeine and spontaneous abortion.

Journal: Epidemiology (Cambridge, Mass.) 20040901

Title: 3beta-20beta-dihydroxy-5alpha-pregnane (UC1011) antagonism of the GABA potentiation and the learning impairment induced in rats by allopregnanolone.

Journal: The European journal of neuroscience 20040901

Title: Influence of the mother's reproductive state on the hormonal status of daughters in marmosets (Callithrix kuhlii).

Journal: American journal of primatology 20040901

Title: Urinary analysis of four testosterone metabolites and pregnanediol by gas chromatography-combustion-isotope ratio mass spectrometry after oral administrations of testosterone.

Journal: Journal of analytical toxicology 20040901

Title: Prenatal diagnosis of P450 oxidoreductase deficiency (ORD): a disorder causing low pregnancy estriol, maternal and fetal virilization, and the Antley-Bixler syndrome phenotype.

Journal: American journal of medical genetics. Part A 20040830

Title: Reproductive physiology and development of artificial insemination technology in killer whales (Orcinus orca).

Journal: Biology of reproduction 20040801

Title: Bayesian analysis of risk factors for anovulation.

Journal: Statistics in medicine 20040630

Title: Body size and ethnicity are associated with menstrual cycle alterations in women in the early menopausal transition: The Study of Women's Health across the Nation (SWAN) Daily Hormone Study.

Journal: The Journal of clinical endocrinology and metabolism 20040601

Title: Prevention of coronary hyperreactivity in preatherogenic menopausal rhesus monkeys by transdermal progesterone.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20040501

Title: Ovarian cycle phase and same-sex mating behavior in Japanese macaque females.

Journal: American journal of primatology 20040501

Title: The role of the endocrine system in baboon maternal behavior.

Journal: Biological psychiatry 20040401

Title: Comparison of three fecal steroid metabolites for pregnancy detection used with single sampling in bighorn sheep (Ovis canadensis).

Journal: Journal of wildlife diseases 20040401

Title: Comparison between creatinine and pregnanediol adjustments in the retrospective analysis of urinary hormone profiles during the human menstrual cycle.

Journal: Clinical chemistry and laboratory medicine 20040101

Title: Differences in the endocrine and behavioral profiles during the peripartum period in macaques.

Journal: Physiology & behavior 20031101

Title: Azasterols as inhibitors of sterol 24-methyltransferase in Leishmania species and Trypanosoma cruzi.

Journal: Journal of medicinal chemistry 20031023

Title: Peripartum sex steroid changes and maternal style in rhesus and Japanese macaques.

Journal: General and comparative endocrinology 20031001

Title: Urinary estrone conjugate and pregnanediol 3-glucuronide enzyme immunoassays for population research.

Journal: Clinical chemistry 20030701

Title: Hormonal monitoring of ovarian activity using the Ovarian Monitor, part I. Validation of home and laboratory results obtained during ovulatory cycles by comparison with radioimmunoassay.

Journal: Steroids 20030501

Title: Comparative study of urinary reproductive hormones in great apes.

Journal: Primates; journal of primatology 20030401

Title: Feasibility of using paper impregnated with urine instead of liquid urine for assessing ovarian activity.

Journal: The Ceylon medical journal 20030301

Title: Rescue of the corpus luteum in human pregnancy.

Journal: Biology of reproduction 20030201

Title: 5alpha-androstane-3alpha,17beta-diol is formed in tammar wallaby pouch young testes by a pathway involving 5alpha-pregnane-3alpha,17alpha-diol-20-one as a key intermediate.

Journal: Endocrinology 20030201

Title: Urinary steroids, FSH and CG measurements for monitoring the ovarian cycle and pregnancy in the chimpanzee.

Journal: Journal of medical primatology 20030201

Title: Purification and characterization of lysozyme-pregnanediol glucuronide conjugates: the effect of the hapten and coupling reagent on the substitution level, sites of acylation and the consequences for the development of future immunoassays.

Journal: Biotechnology and applied biochemistry 20021001

Title: Pregnancy hormone metabolite patterns, pregnancy symptoms, and coffee consumption.

Journal: American journal of epidemiology 20020901

Title: Mean versus individual hormonal profiles in the menstrual cycle.

Journal: Fertility and sterility 20020701

Title: Lowering low density lipoprotein cholesterol with simvastatin, a hydroxy-3-methylglutaryl-coenzyme a reductase inhibitor, does not affect luteal function in premenopausal women.

Journal: The Journal of clinical endocrinology and metabolism 20020701

Title: Estimating the efficacy of emergency contraception--how reliable are the data?

Journal: Contraception 20020701

Title: Luteal phase progesterone excretion in ovulatory women with polycystic ovaries.

Journal: Human reproduction (Oxford, England) 20020601

Title: Relationship between sleep and secretion of gonadotropin and ovarian hormones in women with normal cycles.

Journal: Fertility and sterility 20020401

Title: Caution on the use of saliva measurements to monitor absorption of progesterone from transdermal creams in postmenopausal women.

Journal: Maturitas 20020130

Title: Improved performance of ELISAs for fertility assessment using common reagents and assay protocol as evidence from quality control studies.

Journal: Journal of immunoassay & immunochemistry 20020101

Title: Peripartum sex steroid profiles and endocrine correlates of postpartum maternal behavior in captive gorillas (Gorilla gorilla gorilla).

Journal: Hormones and behavior 20011201

Title: Steroid structure and pharmacological properties determine the anti-amnesic effects of pregnenolone sulphate in the passive avoidance task in rats.

Journal: The European journal of neuroscience 20011201

Title: Studies of molecular structure parameters of 20-piperidin-2-yl-5alpha-pregnan-3beta,20-diol and its N-methyl derivative: two inhibitors of Delta24(25) sterol methyl transferase and Delta24(24') sterol methyl reductase of Trypanosoma cruzi.

Journal: Acta crystallographica. Section B, Structural science 20011001

Title: Hypothalamic-pituitary-ovarian dysfunction after prepubertal chemotherapy and cranial irradiation for acute leukaemia.

Journal: Human reproduction (Oxford, England) 20010901

Title: Effects of covariance model assumptions on hypothesis tests for repeated measurements: analysis of ovarian hormone data and pituitary-pteryomaxillary distance data.

Journal: Statistics in medicine 20010830

Title: Lactational amenorrhea/anovulation and some of their determinants: a comparison of well-nourished and undernourished women.

Journal: Fertility and sterility 20010801

Title: Urinary hormone levels during the natural menstrual cycle: the effect of age.

Journal: The Journal of endocrinology 20010701

Title: Fecal analysis of ovarian cycles in female black-handed spider monkeys (Ateles geoffroyi).

Journal: American journal of primatology 20010601

Title: Longitudinal gonadal steroid excretion in free-living male and female meerkats (Suricata suricatta).

Journal: General and comparative endocrinology 20010501

Title: The effects of peri-ovulatory administration of levonorgestrel on the menstrual cycle.

Journal: Contraception 20010301

Title: [Effects of exposure to low-level benzene and its analogues on reproductive hormone secretion in female workers].

Journal: Zhonghua yu fang yi xue za zhi [Chinese journal of preventive medicine] 20010301

Title: Performance characteristics of a carbon isotope ratio method for detecting doping with testosterone based on urine diols: controls and athletes with elevated testosterone/epitestosterone ratios.

Journal: Clinical chemistry 20010201

Title: H ROBERTSON, et al. Pregnanediol in the urine of the ewe. Nature. 1958 Nov 29;182(4648):1512-3.Sci Total Environ

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Tags:80-92-2 Molecular Formula|80-92-2 MDL|80-92-2 SMILES|80-92-2 5β-Pregnane-3α,20α-diol