MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 462894 | Name: Ambrein

Description:

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

Ambrein is a triterpene alcohol that is the chief constituent of ambergris, a secretion from the digestive system of the sperm whale, and has been suggested as the possible active component producing the supposed aphrodisiac effects of ambergris. It serves as the biological precursor for a number of aromatic derivatives such as ambroxan and is thought to possess fixative properties for other odorants. It has been shown to act as an analgesic and it has been proven to increase sexual behavior in rats, providing some support for its traditional aphrodisiac use. Ambrein has also been shown to decrease spontaneous contractions of smooth muscles in rats, guinea pigs, and rabbits. It is able to reduce these contractions by serving as an antagonist and interfering with the Ca2+ ions from outside of the cell.

Chemical Structure

Ambrein
Ambrein
CAS#473-03-0

Theoretical Analysis

MedKoo Cat#: 462894

Name: Ambrein

CAS#: 473-03-0

Chemical Formula: C30H52O

Exact Mass: 428.4018

Molecular Weight: 428.75

Elemental Analysis: C, 84.04; H, 12.23; O, 3.73

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
Bulk Inquiry
Related CAS #
No Data
Synonym
Ambrein;
IUPAC/Chemical Name
(1R,2R,4aS,8aS)-1-((E)-6-((S)-2,2-dimethyl-6-methylenecyclohexyl)-4-methylhex-3-en-1-yl)-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol
InChi Key
BIADSXOKHZFLSN-RMCJHQKMSA-N
InChi Code
InChI=1S/C30H52O/c1-22(15-16-24-23(2)13-10-18-27(24,3)4)12-9-14-26-29(7)20-11-19-28(5,6)25(29)17-21-30(26,8)31/h12,24-26,31H,2,9-11,13-21H2,1,3-8H3/b22-12+/t24-,25+,26-,29+,30-/m1/s1
SMILES Code
C/C(CC[C@@H]1C(CCCC1(C)C)=C)=C\CC[C@H]2[C@](O)(CC[C@H]3C(C)(CCC[C@]23C)C)C
Appearance
Solid powder
Purity
>98% (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
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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 428.75 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: Ncube EN, Steenkamp L, Dubery IA. Ambrafuran (AmbroxTM) Synthesis from Natural Plant Product Precursors. Molecules. 2020 Aug 25;25(17):E3851. doi: 10.3390/molecules25173851. PMID: 32854176. 2: Rowland SJ, Sutton PA, von der Lühe B, Volkman JK, Vane CH, Ingram SN, Dunn C, Claridge D. Ambrein: a minor, but common constituent of mammalian faeces? Nat Prod Res. 2020 Mar 17:1-6. doi: 10.1080/14786419.2020.1731746. Epub ahead of print. PMID: 32178531. 3: von der Lühe B, Mayes RW, Thiel V, Dawson LA, Graw M, Rowland SJ, Fiedler S. First evidence of terrestrial ambrein formation in human adipocere. Sci Rep. 2019 Dec 4;9(1):18370. doi: 10.1038/s41598-019-54730-w. PMID: 31797886; PMCID: PMC6892809. 4: Moser S, Leitner E, Plocek TJ, Vanhessche K, Pichler H. Engineering of Saccharomyces cerevisiae for the production of (+)-ambrein. Yeast. 2020 Jan;37(1):163-172. doi: 10.1002/yea.3444. Epub 2019 Oct 27. PMID: 31606910. 5: Rowland SJ, Sutton PA, Wolff GA. Biosynthesis of ambrein in ambergris: evidence from isotopic data and identification of possible intermediates. Nat Prod Res. 2019 Jul 30:1-7. doi: 10.1080/14786419.2019.1644630. Epub ahead of print. PMID: 31359775. 6: Wilde MJ, Robson WJ, Sutton PA, Rowland SJ. Volatile and semi-volatile components of jetsam ambergris. Nat Prod Res. 2019 May 14:1-6. doi: 10.1080/14786419.2019.1607855. Epub ahead of print. PMID: 31084225. 7: Rowland SJ, Sutton PA, Knowles TDJ. The age of ambergris. Nat Prod Res. 2019 Nov;33(21):3134-3142. doi: 10.1080/14786419.2018.1523163. Epub 2018 Nov 23. PMID: 30470137. 8: Moser S, Strohmeier GA, Leitner E, Plocek TJ, Vanhessche K, Pichler H. Whole- cell (+)-ambrein production in the yeast Pichia pastoris. Metab Eng Commun. 2018 Aug 16;7:e00077. doi: 10.1016/j.mec.2018.e00077. PMID: 30197866; PMCID: PMC6127371. 9: Rowland SJ, Sutton PA, Belt ST, Fitzsimmons-Thoss V, Scarlett AG. Further spectral and chromatographic studies of ambergris. Nat Prod Res. 2018 Nov;32(21):2603-2609. doi: 10.1080/14786419.2018.1428599. Epub 2018 Jan 22. PMID: 29355034. 10: Ke D, Caiyin Q, Zhao F, Liu T, Lu W. Heterologous biosynthesis of triterpenoid ambrein in engineered Escherichia coli. Biotechnol Lett. 2018 Feb;40(2):399-404. doi: 10.1007/s10529-017-2483-2. Epub 2017 Dec 4. PMID: 29204767. 11: Rowland SJ, Sutton PA. Chromatographic and spectral studies of jetsam and archived ambergris. Nat Prod Res. 2017 Aug;31(15):1752-1757. doi: 10.1080/14786419.2017.1290618. Epub 2017 Feb 16. PMID: 28278659. 12: Ueda D, Hoshino T, Sato T. Cyclization of squalene from both termini: identification of an onoceroid synthase and enzymatic synthesis of ambrein. J Am Chem Soc. 2013 Dec 11;135(49):18335-8. doi: 10.1021/ja4107226. Epub 2013 Nov 27. PMID: 24274794. 13: Raza M, Alorainy MS, Alghasham AA. Evaluation of ambrein and epicoprostanol for their antioxidant properties: protection against adriamycin-induced free radical toxicity. Food Chem Toxicol. 2007 Sep;45(9):1614-9. doi: 10.1016/j.fct.2007.02.024. Epub 2007 Feb 28. PMID: 17408835. 14: Shen YC, Cheng SY, Kuo YH, Hwang TL, Chiang MY, Khalil AT. Chemical transformation and biological activities of ambrein, a major product of ambergris from Physeter macrocephalus (sperm whale). J Nat Prod. 2007 Feb;70(2):147-53. doi: 10.1021/np068029p. PMID: 17315955. 15: Sandroni P. Aphrodisiacs past and present: a historical review. Clin Auton Res. 2001 Oct;11(5):303-7. doi: 10.1007/BF02332975. PMID: 11758796. 16: Yuan A, Huang X, Chen J. [Chemical constituents in aerial part of Ampelopsis grossedentata(Hand.-Mazz.) W.T. Wang]. Zhongguo Zhong Yao Za Zhi. 1998 Jun;23(6):359-60, 383. Chinese. PMID: 11601299. 17: Taha SA, Raza M, El-Khawad IE. Effect of ambrein on smooth muscle responses to various agonists. J Ethnopharmacol. 1998 Feb;60(1):19-26. doi: 10.1016/s0378-8741(97)00126-8. PMID: 9533428. 18: Taha SA, Islam MW, Ageel AM. Effect of ambrein, a major constituent of ambergris, on masculine sexual behavior in rats. Arch Int Pharmacodyn Ther. 1995 Mar-Apr;329(2):283-94. PMID: 8540767. 19: Taha SA, Raza M, Gader AG, Hafeez MA. A study of ambrein treatment for the evaluation of change in plasma biochemical parameters in rats. Jpn J Pharmacol. 1995 Mar;67(3):205-9. doi: 10.1254/jjp.67.205. PMID: 7630038. 20: Taha SA. Studies on the mode of action of ambrein as a new antinociceptive compound. Jpn J Pharmacol. 1992 Oct;60(2):67-71. doi: 10.1254/jjp.60.67. PMID: 1479744.

View History

AM9747

AM9747