beta-SANTALOL

Base Information

• Chemical Name: beta-SANTALOL
• CAS No.: 77-42-9
• Deprecated CAS: 37172-31-9
• Molecular Formula: C15H24 O
• Molecular Weight: 220.355
• European Community (EC) Number: 201-027-2
• UNII: 1JL7K2LW6L
• DSSTox Substance ID: DTXSID70892297
• Nikkaji Number: J152.192F
• Wikipedia: Beta-Santalol
• Wikidata: Q2055416
• Metabolomics Workbench ID: 28444
• ChEMBL ID: CHEMBL3586094
• Mol file: 77-42-9.mol

Synonyms:beta-SANTALOL;beta-Santalenol;Santalol, beta-;2-Methyl-5-(2-methyl-3-methylene-2-norbornyl)-2-penten-1-ol;UNII-1JL7K2LW6L;1JL7K2LW6L;77-42-9;EINECS 201-027-2;(1S-(1alpha,2alpha(Z),4alpha))-2-Methyl-5-(2-methyl-3-methylenebicyclo(2.2.1)hept-2-yl)-2-penten-1-ol;(2Z)-2-methyl-5-[(1S,2R,4R)-2-methyl-3-methylidenebicyclo[2.2.1]hept-2-yl]pent-2-en-1-ol;.beta.-Santalol;2-Penten-1-ol, 2-methyl-5-(2-methyl-3-methylene-2-norbornyl)-;(Z)-beta-santalol;SANTALOL, BETA;[1S-[1alpha,2alpha(Z),4alpha]]-2-methyl-5-(2-methyl-3-methylenebicyclo[2.2.1]hept-2-yl)-2-penten-1-ol;2-Methyl-5-(2-methyl-3-methylenebicyclo(2.2.1)hept-2-yl)-2-penten-1-ol, (1S-(1alpha,2alpha(Z(,4alpha))-;2-Penten-1-ol, 2-methyl-5-(2-methyl-3-methylenebicyclo(2.2.1)hept-2-yl)-, (1S-(1alpha,2alpha(Z),4alpha))-;cis-b-Santalol;cis-beta-santalol;2-Penten-1-ol, 2-methyl-5-((1S,2R,4R)-2-methyl-3-methylenebicyclo(2.2.1)hept-2-yl)-, (2Z)-;2-Penten-1-ol, 2-methyl-5-(2-methyl-3-methylenebicyclo[2.2.1]hept-2-yl)-, [1S-[1alpha,2alpha(Z),4alpha]]-;beta-(Z)-Santalol;(-)-beta-santalol;SANTALOL B;(-)-(z)-beta-santalol;SANTALOL, .BETA.-;SCHEMBL301322;.BETA.-SANTALOL [MI];(-)-.BETA.-SANTALOL;CHEMBL3586094;CHEBI:10441;FEMA 3006;DTXSID70892297;12-BETA-SANTALEN-14-OL;(1S - (1a,2a(Z),4a)) - 2 - methyl - 5 - (2 - methyl - 3 - methylenebicyclo(2.2.1)hept - 2 - yl) -2 - penten - 1 - ol;[1S-[1alpha,2alpha(Z),4alpha]]-2-methyl-5-(2-methyl-3-methylenbicyclo[2.2.1]hept-2-yl)-2-penten-1-ol;2-Penten-1-ol, 2-methyl-5-(2-methyl-3-methylenebicyclo[ 2.2.1]hept-2-yl)-, [1S-[1?,2?(Z),4?]]-;2-Penten-1-ol, 2-methyl-5-(2-methyl-3-methylenebicyclo[2.2.1]hept-2-yl)-, [1.alpha.,2.alpha.(Z),4.alpha.]-(-)-;2-Penten-1-ol, 2-methyl-5-[(1S,2R,4R)-2-methyl-3-methylenebicyclo[2.2.1]hept-2-yl]-, (2Z)-;LMPR0103800003;FEMA NO. 3006, .BETA.-;Q2055416

Chemical Property of beta-SANTALOL

Chemical Property:

• Vapor Pressure: 4.81E-05mmHg at 25°C
• Melting Point: <25 °C
• Refractive Index: nD25 1.5100
• Boiling Point: 312°C at 760 mmHg
• PKA: 14.85±0.10(Predicted)
• Flash Point: 116.3°C
• PSA: 20.23000
• Density: 0.97g/cm³
• LogP: 3.69760
• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 220.182715385
• Heavy Atom Count: 16
• Complexity: 315

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC1(C2CCC(C2)C1=C)C)CO
• Isomeric SMILES: C/C(=C/CC[C@@]1([C@H]2CC[C@H](C2)C1=C)C)/CO
• Uses: (Z)-β-Santalol is a key component of sandalwood oil, which when purified, can be used to suppress lipopolysaccharide-stimulated cytokine/chemokine production in skin cells.

Technology Process of beta-SANTALOL

There total 45 articles about beta-SANTALOL 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: 98.0%

(-)-β-santalyl-acetate (77-43-0) → (-)-(Z)-β-santalol (77-42-9)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 1.5h; optical yield given as %de;

DOI:10.1002/chem.201002729

Reference yield: 50.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 3-(2-Methyl-3-methylenebicyclo<2.2.1>hept-2-yl)propanal (131232-80-9) + ethyltriphenylphosphonium iodide (4736-60-1) → (-)-(Z)-β-santalol (77-42-9)

Guidance literature:

ethyltriphenylphosphonium iodide; With n-butyllithium; In tetrahydrofuran; at -78 ℃;

3-(2-Methyl-3-methylenebicyclo<2.2.1>hept-2-yl)propanal; With n-butyllithium; In tetrahydrofuran; at -78 - 0 ℃;

formaldehyd; In tetrahydrofuran; at 0 - 20 ℃; for 1h;

DOI:10.1002/anie.200903449

Reference yield:

(-)-(1R,3R)-3-methylbicyclo<2.2.1>heptane-2-one (131726-05-1) → (-)-(Z)-β-santalol (77-42-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) 1M sodium bis(trimethylsilyl)amide / 1.) xylene, r.t., 15 min; reflux, 15 min, 2.) xylene, reflux

2: 98 percent / 5percent H₂SO₄ / 4 h / Ambient temperature

3: 1.) 18-crown-6, 0.5M KN(SiMe₃)2 / 1.) THF, toluene, r.t., 1 h, 2.) THF, toluene, -90 deg C up to -60 deg C, 5 h

4: 1.) 1M TiCl₄, Zn / 1.) THF, CH₂Cl₂, r.t., 15 min, 2.) THF, CH₂Cl₂, 11.5 h

5: 24.3 mg / LiAlH₄ / diethyl ether / 5.5 h / Ambient temperature

With lithium aluminium tetrahydride; 18-crown-6 ether; sulfuric acid; sodium hexamethyldisilazane; titanium tetrachloride; potassium hexamethylsilazane; zinc; In diethyl ether;

upstream raw materials:

β-santalene

(1S,2R,4R)-2-Methyl-3-methylene-2-(4-methyl-pent-3-enyl)-bicyclo[2.2.1]heptane

(+)-α-Santalylacetat

ethyl (-)-(Z)-2-methyl-5-<(1S,2R)-2-methyl-3-methylidenebicyclo<2.2.1>hept-2-yl>-2-pentenoate

Downstream raw materials:

(1S,2R,4R)-2-Methyl-3-methylene-2-(4-methyl-pent-3-enyl)-bicyclo[2.2.1]heptane

(1S-endo)-2-methyl-3-methylene-2-(4-methyl-3-pentenyl)-bicyclo[2.2.1]heptane