Ambroxide

Quality 0.50 · 0 views · Updated 2 months ago

Chemical compound

title: "Ambroxide" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["perfume-ingredients", "flavors", "terpenes-and-terpenoids", "tetrahydrofurans", "decalins", "heterocyclic-compounds-with-3-rings"] description: "Chemical compound" topic_path: "general/perfume-ingredients" source: "https://en.wikipedia.org/wiki/Ambroxide" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = | ImageFile = Ambrox.svg | PIN = (3aR,5aS,9aS,9bR)-3a,6,6,9a-Tetramethyldodecahydronaphtho[2,1-b]furan | OtherNames = Ambrox (Firmenich) Ambrofix (Givaudan) Ambroxan (Kao) Ambermox 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 = | CASNo = 100679-85-4 | CASNo2_Ref = | CASNo2 = 3738-00-9 | CASNo2_Comment = (unspecified stereochemistry) | UNII_Ref = | UNII = K60YJF1E9A | ChEMBL_Ref = | ChEMBL = 496447 | ChEBI = 78307 | PubChem = 10857465 | ChemSpiderID = 9032756 | ChemSpiderID_Ref = | 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 = | StdInChIKey = YPZUZOLGGMJZJO-LQKXBSAEBI | StdInChIKey_Ref = | 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 |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. Ambroxide is used in perfumery for creating ambergris notes and as a fixative. Ambroxide has a scent with woody, musky and slightly salty nuances. Another name for ambroxan is ambrocenide. Small amounts (

Synthesis

Ambroxide is synthesized from sclareol, a component of the essential oil of clary sage. Sclareol is oxidatively degraded to a lactone, which is hydrogenated to the corresponding diol. The resulting compound is dehydrated to form ambroxide.

:[[File:Ambroxide synthesis sclareol.svg|thumb|left|500px|Conversion of sclareol to ambroxide]]

References

References

  1. "Apply for a Trademark. Search a Trademark".
  2. Karl-Georg Fahlbusch. (2007). "[[Ullmann's Encyclopedia of Industrial Chemistry]]". Wiley.
  3. "Разница серой амбры и ноты амбры. Синтетические аналоги амбры.".
  4. "Амброценид: химия и аромат в мире парфюмерии".
  5. George A. Burdock. (2010). "Fenaroli's Handbook of Flavor Ingredients". CRC Press.
  6. Brian M Lawrence. (2003). "Essential Oils 1995-2000". Allured Pub..
  7. (2018). "The role of the metal-bound N–H functionality in Noyori-type molecular catalysts". Nature Reviews Chemistry.

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::

perfume-ingredientsflavorsterpenes-and-terpenoidstetrahydrofuransdecalinsheterocyclic-compounds-with-3-rings