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MedKoo Cat#: 462901 | Name: Ambrox

Description:

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

Ambrox is an organic compound of high interest and value in the context of fragrances. It is an important ingredient due to its unique scent and excellent fixative function.

Chemical Structure

Ambrox
Ambrox
CAS#65588-69-4

Theoretical Analysis

MedKoo Cat#: 462901

Name: Ambrox

CAS#: 65588-69-4

Chemical Formula: C15H26O

Exact Mass: 222.1984

Molecular Weight: 222.37

Elemental Analysis: C, 81.02; H, 11.79; O, 7.19

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.
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Related CAS #
No Data
Synonym
Ambrox;
IUPAC/Chemical Name
6,6,9a-trimethyldodecahydronaphtho[2,1-b]furan
InChi Key
IPEPBOBQYDJNON-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H26O/c1-14(2)8-4-9-15(3)11-7-10-16-12(11)5-6-13(14)15/h11-13H,4-10H2,1-3H3
SMILES Code
CC1(CCCC2(C3CCOC3CCC12)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
Ambrox and related ambroxides are highly priced in the fragrance industry, and valued for their delicate odor and fixative properties. Historically, Ambrox was obtained from ambergris, a waxy excretion produced by sperm whales, now an endangered species

Preparing Stock Solutions

The following data is based on the product molecular weight 222.37 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
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PMID: 30197866; PMCID: PMC6127371. 5: Alonso P, Pardo P, Fontaneda R, Fañanás FJ, Rodríguez F. Synthesis and Applications of Cyclohexenyl Halides Obtained by a Cationic Carbocyclisation Reaction. Chemistry. 2017 Sep 21;23(53):13158-13163. doi: 10.1002/chem.201702490. Epub 2017 Aug 23. PMID: 28686348. 6: 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. 7: Fontaneda R, Alonso P, Fañanás FJ, Rodríguez F. Scalable Synthesis of the Amber Odorant 9-epi-Ambrox through a Biomimetic Cationic Cyclization/Nucleophilic Bromination Reaction. Org Lett. 2016 Sep 16;18(18):4626-9. doi: 10.1021/acs.orglett.6b02266. Epub 2016 Sep 2. PMID: 27588550. 8: Yang S, Tian H, Sun B, Liu Y, Hao Y, Lv Y. One-pot synthesis of (-)-Ambrox. Sci Rep. 2016 Sep 1;6:32650. doi: 10.1038/srep32650. PMID: 27581945; PMCID: PMC5007644. 9: Klupinski TP, Strozier ED, Friedenberg DA, Brinkman MC, Gordon SM, Clark PI. Identification of New and Distinctive Exposures from Little Cigars. Chem Res Toxicol. 2016 Feb 15;29(2):162-8. doi: 10.1021/acs.chemrestox.5b00371. Epub 2016 Jan 21. PMID: 26605856; PMCID: PMC4933306. 10: Zerbe P, Bohlmann J. Enzymes for synthetic biology of ambroxide-related diterpenoid fragrance compounds. Adv Biochem Eng Biotechnol. 2015;148:427-47. doi: 10.1007/10_2015_308. PMID: 25846965. 11: Martins MP, Ouazzani J, Arcile G, Jeller AH, de Lima JP, Seleghim MH, Oliveira AL, Debonsi HM, Venâncio T, Yokoya NS, Fujii MT, Porto AL. Biohydroxylation of (-)-ambrox®, (-)-sclareol, and (+)-sclareolide by whole cells of Brazilian marine-derived fungi. Mar Biotechnol (NY). 2015 Apr;17(2):211-8. doi: 10.1007/s10126-015-9610-7. Epub 2015 Jan 30. PMID: 25634054. 12: Schalk M, Pastore L, Mirata MA, Khim S, Schouwey M, Deguerry F, Pineda V, Rocci L, Daviet L. Toward a biosynthetic route to sclareol and amber odorants. J Am Chem Soc. 2012 Nov 21;134(46):18900-3. doi: 10.1021/ja307404u. Epub 2012 Nov 7. PMID: 23113661. 13: Günnewich N, Higashi Y, Feng X, Choi KB, Schmidt J, Kutchan TM. A diterpene synthase from the clary sage Salvia sclarea catalyzes the cyclization of geranylgeranyl diphosphate to (8R)-hydroxy-copalyl diphosphate. Phytochemistry. 2013 Jul;91:93-9. doi: 10.1016/j.phytochem.2012.07.019. Epub 2012 Sep 6. PMID: 22959531. 14: Musharraf SG, Naz S, Najeeb A, Khan S, Choudhary MI. Biotransformation of perfumery terpenoids, (-)-ambrox® by a fungal culture Macrophomina phaseolina and a plant cell suspension culture of Peganum harmala. Chem Cent J. 2012 Aug 5;6(1):82. doi: 10.1186/1752-153X-6-82. PMID: 22863186; PMCID: PMC3551650. 15: Caniard A, Zerbe P, Legrand S, Cohade A, Valot N, Magnard JL, Bohlmann J, Legendre L. Discovery and functional characterization of two diterpene synthases for sclareol biosynthesis in Salvia sclarea (L.) and their relevance for perfume manufacture. BMC Plant Biol. 2012 Jul 26;12:119. doi: 10.1186/1471-2229-12-119. PMID: 22834731; PMCID: PMC3520730. 16: Barrero AF, Herrador MM, Arteaga P, Arteaga JF, Arteaga AF. Communic acids: occurrence, properties and use as chirons for the synthesis of bioactive compounds. Molecules. 2012 Feb 6;17(2):1448-67. doi: 10.3390/molecules17021448. PMID: 22310167; PMCID: PMC6268269. 17: Frija LM, Frade RF, Afonso CA. Isolation, chemical, and biotransformation routes of labdane-type diterpenes. Chem Rev. 2011 Aug 10;111(8):4418-52. doi: 10.1021/cr100258k. Epub 2011 May 27. PMID: 21618966. 18: Hayet E, Fatma B, Souhir I, Waheb FA, Abderaouf K, Mahjoub A, Maha M. Antibacterial and cytotoxic activity of the acetone extract of the flowers of Salvia sclarea and some natural products. Pak J Pharm Sci. 2007 Apr;20(2):146-8. PMID: 17416571. 19: Yang HJ, Li BG, Cai XH, Qi HY, Luo YG, Zhang GL. Chiral decalins: preparation from oleanolic acid and application in the synthesis of (-)-9-epi- ambrox. J Nat Prod. 2006 Nov;69(11):1531-8. doi: 10.1021/np060159a. PMID: 17125216. 20: Nasib A, Musharraf SG, Hussain S, Khan S, Anjum S, Ali S, Atta-Ur-Rahman AU, Choudhary MI. Biotransformation of (-)-ambrox by cell suspension cultures of Actinidia deliciosa. J Nat Prod. 2006 Jun;69(6):957-9. doi: 10.1021/np050221o. PMID: 16792418.