ambroxide

{{short description|Chemical compound}}

{{Chembox

| 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){{cite web|url=http://www.trademarkia.com/ambroxan-78528957.html|title=Apply for a Trademark. Search a Trademark|website=trademarkia.com|access-date=25 February 2018}}
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 = {{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

}}

|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.{{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}} Ambroxide is used in perfumery for creating ambergris notes and as a fixative. Small amounts (< 0.01 ppm) are used as a 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}}