108031-80-7

Basic information

• Product Name: (2S)-(-)-2,2'-OXYBIS(OCTAHYDRO-7,8,8-TRIMETHYL-4,7-METHANOBENZOFURAN)
• Synonyms: (2S)-(-)-2,2'-OXYBIS(OCTAHYDRO-7,8,8-TRIMETHYL-4,7-METHANOBENZOFURAN);(2S)-(-)-2,2'-oxybis(octahydro-7,8,8-trimethyl-4,;2,2'oxybis(octahydro7,8,8-trimethyl-4,7-methanobenzofuran)
• CAS NO: 108031-80-7
• Molecular Formula: C₂₄H₃₈O₃
• Molecular Weight: 374.56
• Mol File: 108031-80-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 149-151 °C(lit.)
• Boiling Point: 435.9°Cat760mmHg
• Flash Point: 148.7°C
• Appearance: /
• Density: 1.12g/cm³
• CAS DataBase Reference: (2S)-(-)-2,2'-OXYBIS(OCTAHYDRO-7,8,8-TRIMETHYL-4,7-METHANOBENZOFURAN)(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-(-)-2,2'-OXYBIS(OCTAHYDRO-7,8,8-TRIMETHYL-4,7-METHANOBENZOFURAN)(108031-80-7)
• EPA Substance Registry System: (2S)-(-)-2,2'-OXYBIS(OCTAHYDRO-7,8,8-TRIMETHYL-4,7-METHANOBENZOFURAN)(108031-80-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 108031-80-7(Hazardous Substances Data)

Usage

Description

(2S)-(-)-2,2'-OXYBIS(OCTAHYDRO-7,8,8-TRIMETHYL-4,7-METHANOBENZOFURAN), commonly known as (-)-Ambrox, is a chemical compound derived from the natural product ambroxan found in the secretion of the ambergris whale. It is a bicyclic sesquiterpene with a pleasant, musky odor, making it a valuable ingredient in perfumery and cosmetic products. Additionally, (-)-Ambrox has potential pharmaceutical applications due to its anti-inflammatory and anti-bacterial properties.

Uses

Used in Perfumery and Cosmetics Industry:
(2S)-(-)-2,2'-OXYBIS(OCTAHYDRO-7,8,8-TRIMETHYL-4,7-METHANOBENZOFURAN) is used as a fragrance ingredient for its pleasant, musky odor, enhancing the overall scent profile of perfumes and cosmetic products.
Used in Fragrance Formulations:
(2S)-(-)-2,2'-OXYBIS(OCTAHYDRO-7,8,8-TRIMETHYL-4,7-METHANOBENZOFURAN) is used as a fixative in fragrance formulations, providing a long-lasting scent and improving the longevity of the fragrance.
Used in Pharmaceutical Applications:
(2S)-(-)-2,2'-OXYBIS(OCTAHYDRO-7,8,8-TRIMETHYL-4,7-METHANOBENZOFURAN) has potential pharmaceutical applications due to its anti-inflammatory and anti-bacterial properties, making it a promising candidate for the development of new therapeutic agents.

Upstream product

• 81925-09-9 (1S,2R,4R,6R,7S)-1,10,10-Trimethyl-3-oxa-tricyclo[5.2.1.0^2,6]decan-4-ol 
• 108031-75-0 (1S,2R,4R,6R,7S)-1,10,10-Trimethyl-3-oxa-tricyclo[5.2.1.0^2,6]decan-4-ol 
• 81969-33-7 (3aR-(3aα,4β,7β,7aα))-3a,4,5,6,7,7a-Hexahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2(3H)-on 
• 108031-76-1 <2R-(2α,3aα,4β,7β,7aα)>-Octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-ol 
• 178969-81-8 [(1S,3R,4R)-3-Hydroxy-4,7,7-trimethyl-bicyclo[2.2.1]hept-(2E)-ylidene]-acetic acid 
• 72690-86-9 2-Hydroxy-2-<(1R)-4,7,7-trimethyl-3-oxobicyclo<2.2.1>hept-2-ylidene>acetic acid 
• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 120687-01-6 <2R-(2α(1S*(2'S*,3a'R*,4'R*,7'R*,7a'R*),2Ξ*),3aα,4β,7β,7aα)>-2,2'-<<2-(Phenylmethoxy)-1-<(phenylmethoxy)methyl>-1,3-propandiyl>bis(oxy)>bis(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran) 
• 81925-09-9 <2S-(2α,3aα,4α,7α,7aα)>-2,3,3a,4,5,6,7,7a-Octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-ol 
• 113775-57-8 <2S-(2α,3aα,4β,7β,7aα)>-2-Methoxy- 
• 120686-94-4 <2R-(2α(2S*(2'S*,3a'R*,4'R*,7'R*,7a'R*),3Ξ*),3aα,4β,7β,7aα)>-2,4-Bis<(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>-1,3-butandiol 

Downstream Products

• 177018-39-2 {[(S)-2-(2,5-Dimethoxy-phenyl)-2-((1R,2R,4S,6R,7R)-1,10,10-trimethyl-3-oxa-tricyclo[5.2.1.0^2,6]dec-4-yloxy)-ethylcarbamoyl]-methyl}-carbamic acid tert-butyl ester 
• 177018-40-5 {[(R)-2-(2,5-Dimethoxy-phenyl)-2-((1R,2R,4S,6R,7R)-1,10,10-trimethyl-3-oxa-tricyclo[5.2.1.0^2,6]dec-4-yloxy)-ethylcarbamoyl]-methyl}-carbamic acid tert-butyl ester 
• 176851-46-0 {[(S)-2-(2,5-Dimethoxy-phenyl)-2-((1R,2R,4S,6R,7R)-1,10,10-trimethyl-3-oxa-tricyclo[5.2.1.0^2,6]dec-4-yloxy)-ethylcarbamoyl]-methyl}-carbamic acid benzyl ester 
• 177018-41-6 {[(R)-2-(2,5-Dimethoxy-phenyl)-2-((1R,2R,4S,6R,7R)-1,10,10-trimethyl-3-oxa-tricyclo[5.2.1.0^2,6]dec-4-yloxy)-ethylcarbamoyl]-methyl}-carbamic acid benzyl ester 
• 263870-65-1 [2R-(2α,3aα,4β,7β,7aα)]-2-(diphenylmethoxy)-octahydro-7,8,8-trimethyl-4,7-methanobenzofuran 
• 263870-60-6 [2R-(2α,3aα,4β,7β,7aα)]-octahydro-7,8,8-trimethyl-2-(phenylmethoxy)-4,7-methanobenzofuran 
• 824952-29-6 [2S-(2α(1R*,2S*),3aα,4β,7β,7aα)]-2-[(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy]-1,2-diphenylethanol 
• 120786-26-7 <2R-(2α(R*,S*),3aα,4β,7β,7aα)>-Octahydro-7,8,8-trimethyl-2-<2,3,4-tris(phenylmethyloxy)butoxy>-4,7-methanobenzofuran 
• 120687-00-5 <2R-(2α(S*,S*),3aα,4β,7β,7aα)>-Octahydro-7,8,8-trimethyl-2-<2,3,4-tris(phenylmethoxy)butoxy>-4,7-methanobenzofuran 
• 197153-86-9 (2R,4S)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-5-((1R,2R,4R,6R,7R)-1,10,10-trimethyl-3-oxa-tricyclo[5.2.1.0^2,6]dec-4-yloxy)-pentanenitrile 
• 197153-88-1 (2S,4S)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-5-((1R,2R,4R,6R,7R)-1,10,10-trimethyl-3-oxa-tricyclo[5.2.1.0^2,6]dec-4-yloxy)-pentanenitrile 

Relevant articles and documents

Chiral lactols, XIV: Stereoselective fusion of five-membered ring lactols to the bornane ring system

Condensation of d-camphor (1) with diethyl oxalate and subsequent ester hydrolysis yielded camphoroxalic acid 3. endo-Fused lactone 9 was obtained by reduction of 3 with zinc followed by reduction with NaBH4 and ring closure with H2SO4. exo-Fused lactone 16, the crystal structure of which was determined, was prepared by reduction of 3 with NaBH4 under basic conditions followed by catalytic hydrogenation and ring closure with HCl. Reduction of 9 and 16 with DI-BALH and application of acidic work-up conditions yielded the self-condensed reduction products (lactol anhydrides) 10 and 17, which are useful reagents in racemate resolution and stereoselective synthesis. VCH Verlagsgesellschaft mbH, 1996.

Chiral Lactols, VIII - A Way for the Asymmetric Induction in the Formation of Sugars

The substituted glycol aldehyde 4 which bears an enantiomerically pure acetal-type protective group exhibiting the configuration of an α-L-sugar at the acetal centre is subjected to aldolization under basic conditions.The resulting products are reduced and characterized by comparison with reference compounds of known absolute configuration.L-Sugars are formed preferentially with L-erythrose being the main product.

Stereoelektronische Effekte und chirale Erkennung: Ein natuerliches Verwandtschaftssystem chiraler Verbindungen basierend auf Selektivitaeten bei der Acetalbildung

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