MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 464268 | Name: Androstenol
Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Androstenol is a steroid pheromone that has been found in boar testes and human male axillary sweat and has diverse biological activities. It enhances GABA-activated currents in primary mouse cerebellar granule cells (EC50 = 0.4 µM). Androstenol (0.1-1 µM) increases the amplitude of GABA-activated currents in HEK293 cells expressing human α1β2γ2 and α2β2γ2 subunit-containing GABAA receptors. In vivo, 5α-androst-16-en-3α-ol (5-10 mg/kg) decreases immobility time in the forced swim test in mice. It increases time spent in the open arms of the elevated plus maze in mice, indicating anxiolytic-like activity, when administered at doses ranging from 30 to 50 mg/kg. Androstenol protects against seizures induced by pentylenetetrazole (PTZ) or electroshock in mice (ED50s = 48.9 and 21.9 mg/kg, respectively).

Chemical Structure

Androstenol
Androstenol
CAS#1153-51-1

Theoretical Analysis

MedKoo Cat#: 464268

Name: Androstenol

CAS#: 1153-51-1

Chemical Formula: C19H30O

Exact Mass: 274.2297

Molecular Weight: 274.45

Elemental Analysis: C, 83.15; H, 11.02; O, 5.83

Price and Availability

Size Price Availability Quantity
10mg USD 350.00 2 Weeks
50mg USD 750.00 2 Weeks
100mg USD 1,050.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
E 281; E281; E-281; NSC 71076; NSC71076; NSC-71076; Androstenol; 5α-Androst-16-en-3α-ol;
IUPAC/Chemical Name
(3R,5S,8R,9S,10S,13R,14S)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
InChi Key
KRVXMNNRSSQZJP-PHFHYRSDSA-N
InChi Code
InChI=1S/C19H30O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,13-17,20H,4-8,10-12H2,1-2H3/t13-,14+,15-,16-,17-,18-,19-/m0/s1
SMILES Code
C[C@@]12[C@@]3([C@]([H])([C@]4([C@](C=CC4)(C)CC3)[H])CC[C@]1(C[C@H](O)CC2)[H])[H]
Appearance
Solid powder
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 274.45 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Gustavson AR, Dawson ME, Bonett DG. Androstenol, a putative human pheromone, affects human (Homo sapiens) male choice performance. J Comp Psychol. 1987 Jun;101(2):210-2. PMID: 3608426. 2: Savic I, Berglund H. Androstenol--a steroid derived odor activates the hypothalamus in women. PLoS One. 2010 Feb 17;5(2):e8651. doi: 10.1371/journal.pone.0008651. PMID: 20174662; PMCID: PMC2822864. 3: Kaminski RM, Marini H, Ortinski PI, Vicini S, Rogawski MA. The pheromone androstenol (5 alpha-androst-16-en-3 alpha-ol) is a neurosteroid positive modulator of GABAA receptors. J Pharmacol Exp Ther. 2006 May;317(2):694-703. doi: 10.1124/jpet.105.098319. Epub 2006 Jan 13. PMID: 16415088. 4: Dufort I, Soucy P, Lacoste L, Luu-The V. Comparative biosynthetic pathway of androstenol and androgens. J Steroid Biochem Mol Biol. 2001 Jun;77(4-5):223-7. doi: 10.1016/s0960-0760(01)00057-7. PMID: 11457660. 5: Fischer J, Wüst M. Quantitative determination of the boar taint compounds androstenone, skatole, indole, 3α-androstenol and 3β-androstenol in wild boars (Sus scrofa) reveals extremely low levels of the tryptophan-related degradation products. Food Chem. 2012 Dec 15;135(4):2128-32. doi: 10.1016/j.foodchem.2012.06.105. Epub 2012 Jul 14. PMID: 22980780. 6: Black SL, Biron C. Androstenol as a human pheromone: no effect on perceived physical attractiveness. Behav Neural Biol. 1982 Mar;34(3):326-30. doi: 10.1016/s0163-1047(82)91711-3. PMID: 7201792. 7: McMullen TP, Lewis RN, McElhaney RN. Comparative differential scanning calorimetric and FTIR and 31P-NMR spectroscopic studies of the effects of cholesterol and androstenol on the thermotropic phase behavior and organization of phosphatidylcholine bilayers. Biophys J. 1994 Mar;66(3 Pt 1):741-52. doi: 10.1016/s0006-3495(94)80850-1. PMID: 8011906; PMCID: PMC1275772. 8: Stefańczyk-Krzymowska S, Wasowska B, Jana B. Boar pheromone androstenol may affect the ovarian morphology in cycling gilts by humoral pathway. Folia Histochem Cytobiol. 2002;40(2):155-6. PMID: 12056622. 9: Crooij MS. Antiprogestins. Eur J Obstet Gynecol Reprod Biol. 1988 Jun;28(2):129-32. doi: 10.1016/0028-2243(88)90091-3. PMID: 3042493. 10: Jacob S, Garcia S, Hayreh D, McClintock MK. Psychological effects of musky compounds: comparison of androstadienone with androstenol and muscone. Horm Behav. 2002 Nov;42(3):274-83. doi: 10.1006/hbeh.2002.1826. PMID: 12460587. 11: Benton D, Wastell V. Effects of androstenol on human sexual arousal. Biol Psychol. 1986 Apr;22(2):141-7. doi: 10.1016/0301-0511(86)90041-4. PMID: 3741936. 12: Jahanfar S, Awang CH, Rahman RA, Samsuddin RD, See CP. Is 3alpha-androstenol pheromone related to menstrual synchrony? J Fam Plann Reprod Health Care. 2007 Apr;33(2):116-8. doi: 10.1783/147118907780254042. PMID: 17407681. 13: Logothetis CJ, Efstathiou E, Manuguid F, Kirkpatrick P. Abiraterone acetate. Nat Rev Drug Discov. 2011 Aug 1;10(8):573-4. doi: 10.1038/nrd3516. PMID: 21804589. 14: Starkenmann C, Mayenzet F, Brauchli R, Troccaz M. 5α-Androst-16-en-3α-ol β-D-glucuronide, precursor of 5α-androst-16-en-3α-ol in human sweat. Chem Biodivers. 2013 Dec;10(12):2197-208. doi: 10.1002/cbdv.201300286. PMID: 24327440. 15: Benton D. The influence of androstenol - a putative human pheromone - on mood throughout the menstrual cycle. Biol Psychol. 1982 Nov-Dec;15(3-4):249-56. doi: 10.1016/0301-0511(82)90047-3. PMID: 6891608. 16: Krzymowski T, Grzegorzewski W, Stefańczyk-Krzymowska S, Skipor J, Wasowska B. Humoral pathway for transfer of the boar pheromone, androstenol, from the nasal mucosa to the brain and hypophysis of gilts. Theriogenology. 1999 Nov;52(7):1225-40. doi: 10.1016/S0093-691X(99)00200-9. PMID: 10735100. 17: Stefańczyk-Krzymowska S, Krzymowski T, Grzegorzewski W, W sowska B, Skipor J. Humoral pathway for local transfer of the priming pheromone androstenol from the nasal cavity to the brain and hypophysis in anaesthetized gilts. Exp Physiol. 2000 Nov;85(6):801-9. doi: 10.1111/j.1469-445x.2000.02056.x. PMID: 11187974. 18: Soucy P, Lacoste L, Luu-The V. Assessment of porcine and human 16-ene- synthase, a third activity of P450c17, in the formation of an androstenol precursor. Role of recombinant cytochrome b5 and P450 reductase. Eur J Biochem. 2003 Mar;270(6):1349-55. doi: 10.1046/j.1432-1033.2003.03508.x. PMID: 12631293. 19: Fischer J, Elsinghorst PW, Bücking M, Tholen E, Petersen B, Wüst M. Development of a candidate reference method for the simultaneous quantitation of the boar taint compounds androstenone, 3α-androstenol, 3β-androstenol, skatole, and indole in pig fat by means of stable isotope dilution analysis-headspace solid-phase microextraction-gas chromatography/mass spectrometry. Anal Chem. 2011 Sep 1;83(17):6785-91. doi: 10.1021/ac201465q. Epub 2011 Aug 15. PMID: 21800819. 20: DINGEMANSE E, HUIS IN T VELD LG, HARTOGH-KATZ SL. Isolation of new androstenol-3()-on-17 from the urine of a patient with adrenal cancer. Nature. 1948 May 29;161(4100):848. doi: 10.1038/161848b0. PMID: 18862128.