{{short description|Chemical compound}} {{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = | ImageFile = Ambrox.svg | PIN = (3a''R'',5a''S'',9a''S'',9b''R'')-3a,6,6,9a-Tetramethyldodecahydronaphtho[2,1-''b'']furan | OtherNames = Ambrox (Firmenich)<br />Ambrofix (Givaudan)<br />Ambroxan (Kao)<ref>{{cite web|url=http://www.trademarkia.com/ambroxan-78528957.html|title=Ambroxan (Registration #3195685) |website=trademarkia.com|access-date=25 February 2018}}</ref><br />Ambermox<br />Ambermor<br />Orcanox<br />(3aR-(3aα,5aβ,9aα,9bβ))-Dodecahydro-3a,6,6,9a-tetra-methylnaphtho(2,1-b)furan;<br />Naphtho(2,1-b)furan, dodecahydro-3a,6,6,9a-tetramethyl-,;<br />8α, 12-Oxido-13,14,15,16-tetranorlabdane;<br />1,5,5,9-Tetramethyl-13-oxatricyclo(8.3.0.0(4,9))tridecane | Section1 = {{Chembox Identifiers | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 100679-85-4 | CASNo2_Ref = {{cascite|correct|CAS}} | CASNo2 = 3738-00-9 | CASNo2_Comment = (unspecified stereochemistry) | UNII_Ref = {{fdacite|correct|FDA}} | UNII = K60YJF1E9A | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 496447 | ChEBI = 78307 | PubChem = 10857465 | ChemSpiderID = 9032756 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | EINECS = 229-861-2 | StdInChI = 1S/C16H28O/c1-14(2)8-5-9-15(3)12(14)6-10-16(4)13(15)7-11-17-16/h12-13H,5-11H2,1-4H3/t12-,13+,15-,16+/m0/s1 | InChI1 = 1S/C16H28O/c1-14(2)8-5-9-15(3)12(14)6-10-16(4)13(15)7-11-17-16/h12-13H,5-11H2,1-4H3/t12-,13+,15-,16+/m0/s1 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = YPZUZOLGGMJZJO-LQKXBSAEBI | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | SMILES = CC1(CCC[C@]2([C@H]1CC[C@@]3([C@@H]2CCO3)C)C)C }} | Section2 = {{Chembox Properties | C=16 | H=28 | O=1 | Density = 0.939 g/cm<sup>3</sup> | RefractIndex = 1.48 | MeltingPtC = 75 | MeltingPt_notes = | BoilingPtC = 120 | BoilingPt_notes= (1.40 mm Hg) | Solubility = insoluble | SolubleOther = soluble | Solvent = ethanol }} | Section7 = {{Chembox Hazards | FlashPtC = 161 }} }}
'''Ambroxide''', widely known by the brand name Ambroxan, is a naturally occurring terpenoid and one of the key constituents responsible for the odor of ambergris. It is an autoxidation product of ambrein.<ref name="perf">{{citation | author=Karl-Georg Fahlbusch | contribution=Flavors and Fragrances | title=Ullmann's Encyclopedia of Industrial Chemistry | edition=7th | publisher=Wiley | year=2007 | page=72|display-authors=etal}}</ref> Ambroxide is used in perfumery for creating ambergris notes and as a fixative.<ref name="perf" /> Ambroxide has a scent with woody, musky and slightly salty nuances.<ref>{{Cite web |title=Разница серой амбры и ноты амбры. Синтетические аналоги амбры. |url=https://syntheticamber.ru/ |access-date=2025-09-11 |website=syntheticamber.ru}}</ref> Small amounts (< 0.01 ppm) are used as a flavoring in food.<ref>{{citation|author=George A. Burdock|title=Fenaroli's Handbook of Flavor Ingredients|page=1895|year=2010|edition=6th|publisher=CRC Press|entry=1,5,5,9-TETRAMETHYL-13-OXATRICYCLO-(8.3.0.0(4,9)) TRIDECANE}}</ref>
The aroma is described as (characteristically) ambergris, sweet, labdanum, dry, woody, pine, cedar, green, and seedy.<ref>{{cite web |title=ambroxan |url=https://scentsandflavors.com/database/9dbb5068-e3d2-4ee0-9b55-1615d35ff7bc |website=Scents and Flavors |publisher=Scents and Flavors |access-date=26 March 2026}}</ref>
== Synthesis == Ambroxide is synthesized from sclareol, a component of the essential oil of clary sage.<ref>{{cite book | title = Essential Oils 1995-2000 | author = Brian M Lawrence | year = 2003 | publisher = Allured Pub. | isbn = 0-931710-94-4}}</ref> Sclareol is oxidatively degraded to a lactone, which is hydrogenated to the corresponding diol.<ref name=Gordon>{{cite journal |doi=10.1038/s41570-018-0049-z|title=The role of the metal-bound N–H functionality in Noyori-type molecular catalysts|year=2018|last1=Dub|first1=Pavel A.|last2=Gordon|first2=John C.|s2cid=106394152|journal=Nature Reviews Chemistry|volume=2|issue=12|pages=396–408}}</ref> The resulting compound is dehydrated to form ambroxide.<ref name="perf" />
:thumb|left|500px|Conversion of sclareol to ambroxide{{clear left}}
== References == {{reflist}}
Category:Perfume ingredients Category:Flavors Category:Terpenes and terpenoids Category:Tetrahydrofurans Category:Decalins Category:Heterocyclic compounds with 3 rings