amber naphthofuran
1,5,5,9-tetramethyl-13-oxatricyclo(8.3.0.0.(4.9))tridecane
Identification
| Name | amber naphthofuran |
| IUPAC | 3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran |
| CAS Number | 3738-00-9 |
| EINECS | 223-118-6 |
| FDA UNII | Search |
| Molecular Formula | C16 H28 O |
| Molecular Weight | 236.39836000 |
| Nikkaji Number | J205.641K |
| CoE Number | 10514 |
Regulatory
| JECFA Food Flavoring | 1240 1,5,5,9-tetramethyl-13-oxatricyclo(8.3.0.0.(4.9))tridecane |
| DG SANTE Food Flavourings | 13.072 1,5,5,9-tetramethyl-13-oxatricyclo(8.3.0.0.(4.9))tridecane |
| FEMA Number | 3471 |
| FDA | No longer provide for the use of these seven synthetic flavoring substances |
Physical Properties
| Appearance | colorless to pale yellow liquid to solid (est) |
| Assay | 96.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 75.00 to 85.00 °C. @ 760.00 mm Hg |
| Boiling Point | 102.00 to 106.00 °C. @ 25.00 mm Hg |
| Acid Value | 1.00 max. KOH/g |
| Vapor Pressure | 0.009000 mmHg @ 25.00 °C. (est) |
| Flash Point | > 212.00 °F. TCC ( > 100.00 °C. ) |
| logP (o/w) | 5.256 (est) |
| Soluble in | alcohol |
| Stability | APC: traces - 1% |
| Similar Items | note |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | perfuming agents |
Organoleptic Properties
| Odor Strength | high , |
| Substantivity | > 400 hour(s) at 10.00 % in dipropylene glycol |
| Odor Description |
at 10.00 % in dipropylene glycol. An elegant amber note with a rich woody character An extremely powerful and elegant amber note An extremely powerful and elegant amber note, more ambery and sharper than CETALOX® Strong amber with dry and woody notes One of the finest ambergris notes, powerful amber, woody odor, which gives rich, elegant effects to all kinds of perfumery beautiful natural aroma components whale ambergris. Sweet, with hints of fresh wood. It has a long diffusion
|
| Odor sample from | Firmenich Inc. |
| Taste Description | amber old wood tobacco powdery dry ambergris animal |
Safety Information
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | flavor and fragrance agents |
| RIFM Fragrance Material Safety Assessment | Search |
| Recommendation for amber naphthofuran usage levels up to | 5.0000 % in the fragrance concentrate. |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | 1.20 (μg/capita/day) |
| Maximised Survey-derived Daily Intakes (MSDI-USA) | 0.10 (μg/capita/day) |
| Structure Class | III |
| baked goods | - |
| beverages(nonalcoholic) | - |
| beverages(alcoholic) | - |
| breakfast cereal | - |
| cheese | - |
| chewing gum | - |
| condiments / relishes | - |
| confectionery froastings | - |
| egg products | - |
| fats / oils | - |
| fish products | - |
| frozen dairy | - |
| fruit ices | - |
| gelatins / puddings | - |
| granulated sugar | - |
| gravies | - |
| hard candy | - |
| imitation dairy | - |
| instant coffee / tea | - |
| jams / jellies | - |
| meat products | - |
| milk products | - |
| nut products | - |
| other grains | - |
| poultry | - |
| processed fruits | - |
| processed vegetables | - |
| reconstituted vegetables | - |
| seasonings / flavors | - |
| snack foods | - |
| soft candy | - |
| soups | - |
| sugar substitutes | - |
| sweet sauces | - |
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Potential Uses
Natural Occurrence
Synonyms
amber naphthofuran
ambermor DL (IFF)
amborl DL
ambrox DL (Firmenich)
cetalor (IFF)
cetalox (Firmenich)
cetalox laevo (Firmenich)
dodecahydro-3a,6,6,9a-tetramethyl naphtho(2,1-beta)furan
dodecahydro-3a,6,6,9a-tetramethylnaphtho(2,1-b)furan
dodecahydro-3a,6,6,9a-tetramethylnaphto-(2,1-b)-furan
dodecahydro-3a-,6,6,9a-tetramethyl(2,1beta)furan
dodecahydrotetramethyl naphthofuran
fixambrene
naphtho(2,1-b)furan, dodecahydro-3a,6,6,9a-tetramethyl-
naphtho[2,1-b]furan, dodecahydro-3a,6,6,9a-tetramethyl-
synambran
tetramethyl dodecahydro-3a,6,6,9a-naphtho(2,1-b)furan
tetramethyl perhydronaphthofurane
1,5,5,9-
tetramethyl-13-oxatricyclo(8.3.0.0.(4.9))tridecane
3a,6,6,9a-
tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran
1,6,10,10-
tetramethyl-5-oxatricyclo[7.4.0.0<2,6>]tridecane
3a,6,6,9a-
tetramethyl-dodecahydro-naphtho[2,1-b]furan
3a,6,6,9a-
tetramethyldodecahydronaphtho[2,1-b]furan
3a,6,6,9a-
tetramethylperhydronaphtho[2,1-b]furan
Info:
Ambrox / Ambroxan
Google Patents:
(+)-Ambrox, process for production thereof and use thereof
US Patents:
8,222,200 - Organic compounds
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.