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ambroxide
ambrox (Firmenich)

Supplier Sponsors

Fragrance Demo Formulas
Name:	6,6,9a-trimethyl-1,2,3a,4,5,5a,7,8,9,9b-decahydrobenzo[e][1]benzofuran
CAS Number:	65588-69-4	3D/inchi
FDA UNII:	Search
Nikkaji Web:	J3.117.851G
XlogP3-AA:	4.50 (est)
Molecular Weight:	222.37142000
Formula:	C15 H26 O
NMR Predictor:	Predict (works with chrome, Edge or firefox)

Category:flavor and fragrance agents

US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:

Google Scholar:	Search
Google Books:	Search
Google Scholar: with word "volatile"	Search
Google Scholar: with word "flavor"	Search
Google Scholar: with word "odor"	Search
Perfumer and Flavorist:	Search
Google Patents:	Search
US Patents:	Search
EU Patents:	Search
Pubchem Patents:	Search
PubMed:	Search
NCBI:	Search

Physical Properties:

Appearance:	colorless clear liquid (est)
Food Chemicals Codex Listed:	No
Melting Point:	168.80 °C. @ 0.00 mm Hg
Boiling Point:	267.00 to 268.00 °C. @ 760.00 mm Hg
Vapor Pressure:	0.013000 mmHg @ 25.00 °C. (est)
Flash Point:	212.00 °F. TCC ( 100.00 °C. )
logP (o/w):	4.975 (est)
Soluble in:
	alcohol
	water, 7.07 mg/L @ 25 °C (est)
Insoluble in:
	water
Stability:
	antiperspirant
	detergent powder
	inorganic acid cleaner
	soap
Similar Items:note
ambroxan
1,5,5,9-tetramethyl-13-oxatricyclo(8.3.0.0.(4.9))tridecane

Organoleptic Properties:

Odor Type: amber

Odor Strength:high ,
recommend smelling in a 1.00 % solution or less

Substantivity:400 hour(s) at 10.00 % in dipropylene glycol

dry amber ambergris paper musk woody cedar pine green seedy

Odor Description:at 1.00 % in dipropylene glycol. dry amber ambergris paper musk woody cedar pine green seedy
Luebke, William tgsc, (1985)

Odor sample from: Firmenich Inc.

Odor and/or flavor descriptions from others (if found).

Cosmetic Information:

None found

Suppliers:

Safety Information:

European information :
Most important hazard(s):
Xi - Irritant
R 36/37/38 - Irritating to eyes, respiratory system, and skin. S 02 - Keep out of the reach of children. S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 36 - Wear suitable protective clothing.

Hazards identification

Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements

Pictogram

Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in Use Information:

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for ambroxide usage levels up to:
	1.0000 % in the fragrance concentrate.

Recommendation for ambroxide flavor usage levels up to:
	30.0000 ppm in the finished product.

Safety References:

EPI System: View

AIDS Citations:Search

Cancer Citations:Search

Toxicology Citations:Search

EPA ACToR:Toxicology Data

EPA Substance Registry Services (SRS):Registry

Laboratory Chemical Safety Summary :196435

National Institute of Allergy and Infectious Diseases:Data

6,6,9a-trimethyl-1,2,3a,4,5,5a,7,8,9,9b-decahydrobenzo[e][1]benzofuran

Chemidplus:0065588694

References:

Leffingwell:	Chirality or Article
	6,6,9a-trimethyl-1,2,3a,4,5,5a,7,8,9,9b-decahydrobenzo[e][1]benzofuran
NIST Chemistry WebBook:	Search Inchi
Pubchem (cid):	196435
Pubchem (sid):	135173255

Other Information:

(IUPAC):	Atomic Weights of the Elements 2011 (pdf)
Videos:	The Periodic Table of Videos
tgsc:	Atomic Weights use for this web site
(IUPAC):	Periodic Table of the Elements
HMDB (The Human Metabolome Database):	Search
Export Tariff Code:	2932.19.0000
Typical G.C.
VCF-Online:	VCF Volatile Compounds in Food
ChemSpider:	View
Wikipedia:	View
EFSA Update of results on the monitoring of furan levels in food:	Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:	Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:	Read Report

Potential Blenders and core components note

For Odor

No odor group found for these

amber romance fragrance
FR

(Z)-iso

ambrettolide
FR

aldehydic

aldehydic

dodecanal (aldehyde C-12 lauric)
FL/FR

2-

methyl undecanal (aldehyde C-12 mna)
FL/FR

10-

undecenal (aldehyde C-11 undecylenic)
FL/FR

amber

(Z)-

amber naphthofuran
FL/FR

amber oxepin
FR

ambergris naphthol
FR

ambergris specialty
FR

ambergris tincture
FL/FR

ambrette seed absolute
FL/FR

ambrette seed oil
FL/FR

ambrette seed oil CO2 extract
FL/FR

ambrette seed oil replacer
FR

alpha-

angelica root oil
FL/FR

cistus ladaniferus absolute resin
FL/FR

cistus ladaniferus resinoid
FL/FR

(cis+trans)-6,6a,7,8,9,9a-

hexahydro-7,7,8,9,9-pentamethyl-5H-cyclopenta[H]quinazoline
FR

labdanum oil
FL/FR

animal

animal carbolactone
FR

costus valerolactone
FR

2-

methyl-4-(camphenyl-8) cyclohexanone
FR

musk indenofuran
FR

balsamic

amyris wood oil
FL/FR

siam

benzoin resinoid
FL/FR

oriental specialty
FR

berry

raspberry ketone
FL/FR

caramellic

ethyl maltol
FL/FR

immortelle absolute
FL/FR

maltol
FL/FR

coconut

gamma-

nonalactone (aldehyde C-18 (so-called))
FL/FR

gamma-

octalactone
FL/FR

earthy

fatty

floral

acetophenone
FL/FR

iso

amyl salicylate
FL/FR

bois de rose oil brazil
FL/FR

iso

butyl salicylate
FL/FR

cyclamen aldehyde
FL/FR

dihydrojasmone
FL/FR

floral pyranol
FR

heliotropyl acetone
FL/FR

alpha-

hexyl cinnamaldehyde
FL/FR

laevo-

methyl dihydrojasmonate
FL/FR

ocean propanal
FL/FR

phenethyl phenyl acetate
FL/FR

fruity

gamma-

decalactone
FL/FR

gamma-

undecalactone (aldehyde C-14 (so-called))
FL/FR

valeriana officinalis root extract
FL/FR

green

diphenyl oxide
FL/FR

galbanum oil
FL/FR

methyl heptine carbonate
FL/FR

(E,Z)-2,6-

nonadien-1-ol
FL/FR

violet leaf absolute
FL/FR

hay

beeswax absolute
FL/FR

herbal

daucus carota fruit oil
FL/FR

melon

melon heptenal
FL/FR

(Z)-6-

watermelon ketone
FR

mossy

veramoss (IFF)
FR

musk

musk decanolide
FR

musk indanone
FR

musk lactone
FR

musk methyl ketone
FR

6,7,8,9-

tetrahydro-7,7,8,9,9-pentamethyl-5H-cyclopenta[H]quinazoline
FR

spicy

cassia bark oil china
FL/FR

black

currant bud absolute
FL/FR

terpenic

frankincense oil
FL/FR

tonka

tonka bean absolute
FR

waxy

1-

dodecanol
FL/FR

ethyl laurate
FL/FR

woody

acetyl cedrene
FR

amber dodecane
FR

cistus ladaniferus gum
FR

cistus twig/leaf oil
FL/FR

guaiacwood oil
FL/FR

gurjun balsam oil
FR

hydroxyambran
FR

labdanum concrete
FR

methyl 2,6,10-trimethyl cyclododeca-2,5,9-trienyl ketone
FR

methyl cedryl ketone
FL/FR

delta-

methyl ionone
FL/FR

patchouli ethanone
FR

patchouli oil
FL/FR

sandal pentenol
FL/FR

sclareolide
FL/FR

spruce needle oil canada
FL/FR

woody acetate
FR

For Flavor

No flavor group found for these

ambergris tincture
FL/FR

cistus ladaniferus resinoid
FL/FR

delta-

methyl ionone
FL/FR

sandal pentenol
FL/FR

amber

amber

amber naphthofuran
FL/FR

ambrette seed oil
FL/FR

ambrette seed oil CO2 extract
FL/FR

alpha-

cistus ladaniferus absolute resin
FL/FR

labdanum oil
FL/FR

apple

(E,Z)-2,6-

nonadien-1-ol
FL/FR

balsamic

siam

benzoin resinoid
FL/FR

berry

heliotropyl acetone
FL/FR

raspberry ketone
FL/FR

brown

beeswax absolute
FL/FR

caramellic

caramel furanone
FL

ethyl maltol
FL/FR

maltol
FL/FR

citrus

laevo-

coconut

gamma-

nonalactone (aldehyde C-18 (so-called))
FL/FR

cooling

iso

butyl salicylate
FL/FR

creamy

gamma-

undecalactone (aldehyde C-14 (so-called))
FL/FR

earthy

fatty

10-

undecenal (aldehyde C-11 undecylenic)
FL/FR

floral

bois de rose oil brazil
FL/FR

dihydrojasmone
FL/FR

methyl dihydrojasmonate
FL/FR

ocean propanal
FL/FR

fruity

gamma-

decalactone
FL/FR

valeriana officinalis root extract
FL/FR

green

iso

amyl salicylate
FL/FR

angelica root oil
FL/FR

cyclamen aldehyde
FL/FR

diphenyl oxide
FL/FR

galbanum oil
FL/FR

immortelle absolute
FL/FR

melon heptenal
FL/FR

methyl heptine carbonate
FL/FR

(Z)-6-

violet leaf absolute
FL/FR

herbal

daucus carota fruit oil
FL/FR

honey

phenethyl phenyl acetate
FL/FR

lactonic

gamma-

octalactone
FL/FR

powdery

acetophenone
FL/FR

soapy

dodecanal (aldehyde C-12 lauric)
FL/FR

1-

dodecanol
FL/FR

spicy

cassia bark oil china
FL/FR

black

currant bud absolute
FL/FR

waxy

ethyl laurate
FL/FR

alpha-

hexyl cinnamaldehyde
FL/FR

2-

methyl undecanal (aldehyde C-12 mna)
FL/FR

woody

(Z)-

ambrette seed absolute
FL/FR

amyris wood oil
FL/FR

cistus twig/leaf oil
FL/FR

frankincense oil
FL/FR

guaiacwood oil
FL/FR

methyl cedryl ketone
FL/FR

patchouli oil
FL/FR

sclareolide
FL/FR

spruce needle oil canada
FL/FR

Potential Uses:

FR	agate
FR	amber
FR	ambergris
FR	ambreine
FR	ambrette oil replacer
FR	animal
FR	baby powder
FR	balsam
FR	bay rum
FR	bayberry
FR	blackberry
FR	blue grass
FR	blueberry
FR	bouquet
FR	cabreuva wood
FR	castoreum
FR	cedar forest
FR	christmas
FR	cigar
FR	clean linen
FR	coronilla
FR	deertongue absolute replacer
	dry
FR	earth
	fantasy blends
FR	fern
FR	fir balsam
FR	floral
FL/FR	guaiacwood
FR	habuba
FR	hay new mown hay
FR	heather
FR	herbal
FR	hollyberry
FR	incense
FR	juniper berry
FR	labdanum
FR	leather
FR	leather russian leather
FR	maja
FR	moss
FR	musk
FR	ocean sea
FR	oriental
	paper
FR	patchouli
FR	pine forest
FR	powder
FR	rain
FR	raspberry
FR	sandalwood
FR	sea breeze
FR	spice
FR	spring rain
FR	sweet grass
FL	tea
FR	tobacco
FR	tonka bean
	tweed
FR	vanilla
FR	woodruff
FR	woody

Occurrence (nature, food, other):note

cistus oil @ 1.4%
Data GC Search Trop Picture

Synonyms:

	amberlyn (Quest)
	amberlyn super (Quest)
	amberox DL
	ambrox (Firmenich)
	dodecahydro-3alpha,6,6,9alpha-tetramethyl naphtho 2,1-beta furan
3alpha,6,6,9alpha-per	hydrotetramethyl naphtho(2,1-beta)furan
1,5,5,9-	tetramethyl-13-oxatricyclo(8.3.0.0)(4,9)tridecane
6,6,9a-	trimethyl-1,2,3a,4,5,5a,7,8,9,9b-decahydrobenzo[e][1]benzofuran
6,6,9a-	trimethyl-1,2,3a,4,5,5a,7,8,9,9b-decahydronaphtho[2,1-b]furan

Articles:

PubMed:Toward a biosynthetic route to sclareol and amber odorants.

PubMed:A diterpene synthase from the clary sage Salvia sclarea catalyzes the cyclization of geranylgeranyl diphosphate to (8R)-hydroxy-copalyl diphosphate.

PubMed:Biotransformation of perfumery terpenoids, (-)-ambrox® by a fungal culture Macrophomina phaseolina and a plant cell suspension culture of Peganum harmala.

PubMed:Discovery and functional characterization of two diterpene synthases for sclareol biosynthesis in Salvia sclarea (L.) and their relevance for perfume manufacture.

PubMed:Communic acids: occurrence, properties and use as chirons for the synthesis of bioactive compounds.

PubMed:Isolation, chemical, and biotransformation routes of labdane-type diterpenes.

PubMed:Antibacterial and cytotoxic activity of the acetone extract of the flowers of Salvia sclarea and some natural products.

PubMed:Chiral decalins: preparation from oleanolic acid and application in the synthesis of (-)-9-epi-ambrox.

PubMed:Biotransformation of (-)-ambrox by cell suspension cultures of Actinidia deliciosa.

PubMed:Chiral proton donor reagents: tin tetrachloride--coordinated optically active binaphthol derivatives.

PubMed:Enantio- and diastereoselective stepwise cyclization of polyprenoids induced by chiral and achiral LBAs. A new entry to (-)-ambrox, (+)-podocarpa-8,11,13-triene diterpenoids, and (-)-tetracyclic polyprenoid of sedimentary origin.

PubMed:Oxidative metabolism of ambrox and sclareolide by Botrytis cinerea.

Notes:

None found

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