# Ambroxide
> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Ambroxide
> Markdown URL: https://mediated.wiki/source/Ambroxide.md
> Source: https://en.wikipedia.org/wiki/Ambroxide
> Source revision: 1356696236
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)
{{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](/source/Firmenich))
Ambrofix ([Givaudan](/source/Givaudan))
Ambroxan (Kao)[{{cite web|url=http://www.trademarkia.com/ambroxan-78528957.html|title=Ambroxan (Registration #3195685) |website=trademarkia.com|access-date=25 February 2018}}]
Ambermox
Ambermor
Orcanox
(3aR-(3aα,5aβ,9aα,9bβ))-Dodecahydro-3a,6,6,9a-tetra-methylnaphtho(2,1-b)furan;
Naphtho(2,1-b)furan, dodecahydro-3a,6,6,9a-tetramethyl-,;
8α, 12-Oxido-13,14,15,16-tetranorlabdane;
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/cm3
| RefractIndex = 1.48
| MeltingPtC = 75
| MeltingPt_notes =
| BoilingPtC = 120
| BoilingPt_notes= (1.40 mm Hg)
| Solubility = insoluble
| SolubleOther = soluble
| Solvent = [ethanol](/source/ethanol)
}}
| Section7 = {{Chembox Hazards
| FlashPtC = 161
}}
}}
'''Ambroxide''', widely known by the brand name Ambroxan, is a naturally occurring [terpenoid](/source/terpenoid) and one of the key constituents responsible for the odor of [ambergris](/source/ambergris). It is an [autoxidation](/source/autoxidation) product of [ambrein](/source/ambrein).[{{citation | author=Karl-Georg Fahlbusch | contribution=Flavors and Fragrances | title=[Ullmann's Encyclopedia of Industrial Chemistry](/source/Ullmann's_Encyclopedia_of_Industrial_Chemistry) | edition=7th | publisher=Wiley | year=2007 | page=72|display-authors=etal}}] Ambroxide is used in [perfume](/source/perfume)ry for creating [ambergris](/source/ambergris) notes and as a [fixative](/source/Fixative_(perfumery)).[{{Cite web |title=Разница серой амбры и ноты амбры. Синтетические аналоги амбры. |url=https://syntheticamber.ru/ |access-date=2025-09-11 |website=syntheticamber.ru}}] Small amounts (< 0.01 ppm) are used as a [flavoring](/source/flavoring) in food.[{{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}}]
The aroma is described as (characteristically) ambergris, sweet, labdanum, dry, woody, pine, cedar, green, and seedy.[{{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}}]
== Synthesis ==
Ambroxide is synthesized from [sclareol](/source/sclareol), a component of the [essential oil](/source/essential_oil) of [clary sage](/source/Salvia_sclarea).[{{cite book | title = Essential Oils 1995-2000 | author = Brian M Lawrence | year = 2003 | publisher = Allured Pub. | isbn = 0-931710-94-4}}] Sclareol is oxidatively degraded to a [lactone](/source/lactone), which is [hydrogenated](/source/Hydrogenation) to the corresponding [diol](/source/diol).[{{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}}] The resulting compound is [dehydrated](/source/Dehydration_reaction) to form ambroxide.