Ambroxan

Base Information

• Chemical Name: Ambroxan
• CAS No.: 6790-58-5
• Deprecated CAS: 31207-71-3,254762-72-6,301677-29-2,435274-92-3,254762-72-6
• Molecular Formula: C16H28O
• Molecular Weight: 236.398
• Hs Code.: 2932999099
• European Community (EC) Number: 229-861-2
• UNII: TD34B3O8M9,K60YJF1E9A
• DSSTox Substance ID: DTXSID0047113
• Nikkaji Number: J14.107K
• Wikipedia: Ambroxide
• Wikidata: Q2793438
• RXCUI: 2557381
• ChEMBL ID: CHEMBL496447
• Mol file: 6790-58-5.mol

Synonyms:ambrox

Chemical Property of Ambroxan

Chemical Property:

• Appearance/Colour: white crystals
• Vapor Pressure: 0.00934mmHg at 25°C
• Melting Point: 73-77 °C
• Refractive Index: 1.48
• Boiling Point: 273.9 °C at 760 mmHg
• Flash Point: 104.8 °C
• PSA: 9.23000
• Density: 0.939 g/cm³
• LogP: 4.40800
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: 1.88mg/L at 20℃
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 236.214015512
• Heavy Atom Count: 17
• Complexity: 322

Purity/Quality:

98%, ^*data from raw suppliers

(-)-Ambroxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(CCCC2(C1CCC3(C2CCO3)C)C)C
• Isomeric SMILES: C[C@]12CCCC([C@@H]1CC[C@@]3([C@@H]2CCO3)C)(C)C
• Description: Ambroxan is a synthetic spice with the special aroma of natural ambergris, and it is recognized as one of the best substitutes for natural ambergris. It is one of the most critical trace components of natural ambergris tincture. Natural ambergris is a precious animal spice. It is a kind of stone in the stomach of sperm whale. It is vomited or excreted on the sea surface by the whale, and it emits a special fragrance in the air for a long time.
• Uses: (-)-Ambroxide can be used:To prepare (+)-sclareolide through C-H oxidation strategy.As a substrate in C(sp3)-H alkylation/arylation studies of ethers.As a substrate in the study of ethereal hydrocarbon hydroperoxidation using singlet O2.

Technology Process of Ambroxan

There total 437 articles about Ambroxan which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(d,l)-13,14,15,16-tetranor-8α,12-epoxy-2-labdene → (±)-ambrox (3738-00-9,6790-58-5,67844-43-3,68365-88-8,68365-89-9,100679-85-4,105561-31-7,108945-29-5,119818-38-1,122566-15-8,122566-16-9,122566-18-1,124578-52-5,131831-61-3,131831-62-4,131831-63-5,133907-53-6,138283-79-1,138283-80-4,145164-17-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; under 760 Torr;

DOI:10.1021/jo980211a

Reference yield: 75.0%

(Z)-4-Methyl-6-(2',6',6'-trimethyl-1'-cyclohexenyl)hex-3-en-1-ol (110202-08-9) → (3aRS,5aRS,9aRS,9bSR)-dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan (3738-00-9,6790-58-5,67844-43-3,68365-88-8,68365-89-9,100679-85-4,105561-31-7,108945-29-5,119818-38-1,122566-15-8,122566-16-9,122566-18-1,124578-52-5,131831-61-3,131831-62-4,131831-63-5,133907-53-6,138283-79-1,138283-80-4,145164-17-6) + (±)-ambrox (3738-00-9,6790-58-5,67844-43-3,68365-88-8,68365-89-9,100679-85-4,105561-31-7,108945-29-5,119818-38-1,122566-15-8,122566-16-9,122566-18-1,124578-52-5,131831-61-3,131831-62-4,131831-63-5,133907-53-6,138283-79-1,138283-80-4,145164-17-6) + (3aR,5aR,9aR,9bR)-3a,6,6,9a-Tetramethyl-dodecahydro-naphtho[2,1-b]furan + (3aRS,5aSR,9aSR,9bSR)-dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan (3738-00-9,6790-58-5,67844-43-3,68365-88-8,68365-89-9,100679-85-4,105561-31-7,108945-29-5,119818-38-1,122566-15-8,122566-16-9,122566-18-1,124578-52-5,131831-61-3,131831-62-4,131831-63-5,133907-53-6,138283-79-1,138283-80-4,145164-17-6)

Guidance literature:

With chlorosulfonic acid; 1-Nitropropane; at -78 ℃; for 0.15h; Further byproducts given. Yields of byproduct given;

DOI:10.1021/jo951908o

Reference yield: 75.0%

(Z)-4-Methyl-6-(2',6',6'-trimethyl-1'-cyclohexenyl)hex-3-en-1-ol (110202-08-9) → (3aRS,5aRS,9aRS,9bSR)-dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan (3738-00-9,6790-58-5,67844-43-3,68365-88-8,68365-89-9,100679-85-4,105561-31-7,108945-29-5,119818-38-1,122566-15-8,122566-16-9,122566-18-1,124578-52-5,131831-61-3,131831-62-4,131831-63-5,133907-53-6,138283-79-1,138283-80-4,145164-17-6) + (±)-ambrox (3738-00-9,6790-58-5,67844-43-3,68365-88-8,68365-89-9,100679-85-4,105561-31-7,108945-29-5,119818-38-1,122566-15-8,122566-16-9,122566-18-1,124578-52-5,131831-61-3,131831-62-4,131831-63-5,133907-53-6,138283-79-1,138283-80-4,145164-17-6) + (3aR,5aR,9aR,9bR)-3a,6,6,9a-Tetramethyl-dodecahydro-naphtho[2,1-b]furan + (3aRS,5aSR,9aSR,9bSR)-dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan (3738-00-9,6790-58-5,67844-43-3,68365-88-8,68365-89-9,100679-85-4,105561-31-7,108945-29-5,119818-38-1,122566-15-8,122566-16-9,122566-18-1,124578-52-5,131831-61-3,131831-62-4,131831-63-5,133907-53-6,138283-79-1,138283-80-4,145164-17-6)

Guidance literature:

With chlorosulfonic acid; 1-Nitropropane; at -78 ℃; for 0.15h; Further byproducts given. Yields of byproduct given;

DOI:10.1021/jo951908o

upstream raw materials:

2-((1'R,4'aS,8'aS)-5',5',8'a-Trimethyl-octahydro-spiro[[1,3]dioxolane-2,2'-naphthalen]-1'-yl)-ethanol

(1R,2S,4aS,8aS)-1-(2-Benzyloxy-ethyl)-2,5,5,8a-tetramethyl-decahydro-naphthalen-2-ol

(1S,4aS,8aS)-1-(2-Benzyloxy-ethyl)-5,5,8a-trimethyl-octahydro-naphthalen-2-one

(1R,4aS,8aS)-1-(2-Benzyloxy-ethyl)-5,5,8a-trimethyl-octahydro-naphthalen-2-one

Downstream raw materials:

(3aRS,5aSR,9aRS,9bSR)-dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan

(-)-norlabdane

<3aR-(3aα,4α,6aα,10aS^*)> dodecahydro-3a,4,7,7-tetramethyl-2H-naphtho<8a,1-b>furan

(3aR)-(+)-sclareolide

Refernces

• 1、 Hinder,Stoll. "-". . . Retrieved 1954.
• 2、 -. "METHOD FOR SYNTHESISING AMBROXIDE FROM AGERATINA JOCOTEPECANA". Paragraph 0058; 0059. . Retrieved 2019/02/05.
• 3、 -. "A drop of the fragrant ether perfuming preparation method". Paragraph 0033-0034. . Retrieved 2017/08/25.