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ambroxide

Ambroxide is a flavor and fragrance compound known for a potent amber odor resembling ambergris with extensive use in perfumery and flavoring.

General Material Description

Ambroxide (PubChem CID 196435) is a synthetic organic compound classified chemically as a polycyclic ether with the molecular formula C15H26O and a molecular weight of approximately 222.37 g/mol. It appears as a colorless to pale yellow liquid notable for its strong amber odor reminiscent of natural ambergris. The compound is also referred to using synonyms such as 6,6,9a-trimethyl-1,2,3a,4,5,5a,7,8,9,9b-decahydrobenzo[e][1]benzofuran and amberox DL. Ambroxide is derived synthetically, often employed as a fragrance ingredient and flavoring agent. It is also a component of essential oils like cistus oil, where it occurs at low concentrations. Its stable nature and characteristic scent profile make it important in perfumery and flavor formulation.

Occurrence, Applicability & Potential Uses

Ambroxide naturally occurs in certain essential oils, notably cistus oil, where it contributes approximately 1.4% of the composition. This origin links it to labdanum, a source known for rich amber notes. Ambroxide is widely used in flavor and fragrance industries to impart durable ambergris and woody amber aromas into products. Its applications include creating complex perfume accords invoking amber, cedarwood, musk, and balsamic impressions. The compound's use aligns with safety guidelines such as the IFRA (Global) Code of Practice, which recommends maximum concentration limits to manage consumer exposure.

Physico-Chemical Properties Summary

Ambroxide exhibits significant lipophilicity with an estimated logP value near 5, indicating preferential solubility in organic solvents over water. It is a colorless liquid boiling between 267 and 268°C at atmospheric pressure, reflecting relatively low volatility. The vapor pressure is very low at room temperature (about 0.013 mmHg at 25°C), supporting its substantivity in formulations. Ambroxide dissolves readily in alcohol but has minimal solubility in water, approximately 7 mg/L at 25°C. The compound has a flash point of about 100°C, indicating moderate flammability precautions. These attributes influence its function in fragrance blends, favoring stability and sustained release in diverse matrices.

FAQ

What is ambroxide and what are its main characteristics?
Ambroxide is a synthetic fragrance and flavor compound known chemically as 6,6,9a-trimethyl-1,2,3a,4,5,5a,7,8,9,9b-decahydrobenzo[e][1]benzofuran with molecular formula C15H26O. It features a potent amber odor reminiscent of ambergris, often described with woody, musky, and balsamic nuances. Ambroxide typically appears as a colorless to pale yellow liquid and is widely used to impart ambergris-like aroma in perfumery and flavor applications.
Where does ambroxide occur naturally and how is it commonly applied?
Ambroxide occurs naturally as a minor component in essential oils such as cistus oil, which is related to labdanum resins. Its primary use is as a flavor and fragrance ingredient, contributing amber, woody, and musky scents to consumer products. Due to its stability and long-lasting scent profile, it is incorporated into perfumes, scented products, and certain flavor formulations like tea and guaiacwood flavors.
What safety and regulatory guidelines apply to ambroxide use?
Ambroxide's safety is evaluated under frameworks such as the IFRA Code of Practice (Global), which governs its maximum use levels in fragrance and flavor products. For fragrances, usage is generally limited to 1.0% concentration in concentrates, while flavor use may be up to 30 ppm in finished goods. While classified as an irritant under certain European regulations, no specific hazard classifications apply according to OSHA's Hazard Communication Standard (GHS). Careful adherence to recommended use levels helps mitigate potential risks.

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & 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
Publications by PubMed
Toward a biosynthetic route to sclareol and amber odorants.
A diterpene synthase from the clary sage Salvia sclarea catalyzes the cyclization of geranylgeranyl diphosphate to (8R)-hydroxy-copalyl diphosphate.
Biotransformation of perfumery terpenoids, (-)-ambrox® by a fungal culture Macrophomina phaseolina and a plant cell suspension culture of Peganum harmala.
Discovery and functional characterization of two diterpene synthases for sclareol biosynthesis in Salvia sclarea (L.) and their relevance for perfume manufacture.
Communic acids: occurrence, properties and use as chirons for the synthesis of bioactive compounds.
Isolation, chemical, and biotransformation routes of labdane-type diterpenes.
Antibacterial and cytotoxic activity of the acetone extract of the flowers of Salvia sclarea and some natural products.
Chiral decalins: preparation from oleanolic acid and application in the synthesis of (-)-9-epi-ambrox.
Biotransformation of (-)-ambrox by cell suspension cultures of Actinidia deliciosa.
Chiral proton donor reagents: tin tetrachloride--coordinated optically active binaphthol derivatives.
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.
Oxidative metabolism of ambrox and sclareolide by Botrytis cinerea.

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

General Material Information

Preferred name ambroxide
Trivial Name 6,6,9a-trimethyl-1,2,3a,4,5,5a,7,8,9,9b-decahydrobenzo[e][1]benzofuran
Short Description ambrox (Firmenich)
Formula C15 H26 O
CAS Number 65588-69-4
FDA UNII Search
Nikkaji Number J3.117.851G
xLogP3-AA 4.50 (est)
NMR Predictor External link
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

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 222.37141418457
Boiling Point 267 to 268°C @ 760 mm Hg
Vapor Pressure 0.013 mmHg @ 25 °C
Flash Point TCC Value 100 °C TCC
logP (o/w) 4.975 est
Solubility
alcohol Yes
water, 7.07 mg/L @ 25 °C (est) Yes
water No
Stability
antiperspirant Unspecified
detergent powder Unspecified
inorganic acid cleaner Unspecified
soap Unspecified

Organoleptic Properties

Odor Type: Amber
dry, amber, ambergris, paper, musk, woody, cedar, pine, green, seedy
Odor strength high , recommend smelling in a 1.00 % solution or less
Substantivity 400 hour(s) at 10.00 % in dipropylene glycol
Luebke, William tgsc, (1985) At 1.00 % in dipropylene glycol. dry amber ambergris paper musk woody cedar pine green seedy

Occurrences

Safety Information

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
WGK Germany:1
6,6,9a-trimethyl-1,2,3a,4,5,5a,7,8,9,9b-decahydrobenzo[e][1]benzofuran
Chemidplus:0065588694