Sabinene

Base Information

• Chemical Name: Sabinene
• CAS No.: 3387-41-5
• Molecular Formula: C₁₀H₁₆
• Molecular Weight: 136.237
• European Community (EC) Number: 222-212-4
• NSC Number: 407278
• Nikkaji Number: J7.728C
• Wikipedia: Sabinene
• Wikidata: Q421278
• NCI Thesaurus Code: C107280,C73928
• RXCUI: 1309293
• Metabolomics Workbench ID: 135107
• ChEMBL ID: CHEMBL452687
• Mol file: 3387-41-5.mol

Synonyms:sabinene;sabinene, (1R)-isomer

Chemical Property of Sabinene

Chemical Property:

• Vapor Pressure: 2.63mmHg at 25°C
• Refractive Index: 1.483
• Boiling Point: 163.999 °C at 760 mmHg
• Flash Point: 36.667 °C
• PSA: 0.00000
• Density: 0.89 g/cm³
• LogP: 2.99870
• Storage Temp.: 2-8°C
• Water Solubility.: 5.03mg/L at 20℃
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 136.125200510
• Heavy Atom Count: 10
• Complexity: 179

Purity/Quality:

98% min ^*data from raw suppliers

Sabinene(70%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R10-23/25:
• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 16-26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C12CCC(=C)C1C2
• Description: Sabinene is a bicyclic monoterpene found in a variety of plants, including Cannabis, that has antifungal and anti-inflammatory properties. It inhibits the growth of various fungi in vitro, including several species of Candida, Trichophyton, and Aspergillus (MICs = 0.16-5 μl/ml). Sabinene (0.32 μl/ml) prevents increases in nitrite production in RAW 264.7 macrophages stimulated by LPS and IFN-γ. It is cytotoxic to RAW 264.7 macrophages and HaCat keratinocytes when used at a concentration of 1.25 μl/ml. Formulations containing sabinene have been used as perfume additives.

Technology Process of Sabinene

There total 7 articles about Sabinene 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:

geranyl diphosphate (763-10-0) → 3,7-dimethylocta-1,6-dien-3-ol (78-70-6) + 7-methyl-3-methene-1,6-octadiene (123-35-3) + Geraniol (106-24-1) + Terpinolene (586-62-9,69073-38-7) + terpineol (98-55-5,2438-12-2) + sabinene (2009-00-9,10408-16-9,15826-80-9,3387-41-5) + α-thujene (563-34-8,2867-05-2,3917-48-4,75715-79-6) + (-)-(S)-limonene (5989-54-8,555-08-8,8022-90-0,9003-73-0,95327-98-3)

Guidance literature:

With sodium tungstate; recombinant terpene synthases TPS₄-B₇₃ from Zea mays; sodium fluoride; magnesium chloride; In pentane; at 30 ℃; for 0.333333h; pH=7; Reagent/catalyst; Inert atmosphere; Enzymatic reaction;

DOI:10.1039/c4cc10395e

Reference yield:

geranyl diphosphate (763-10-0) → Beta-pinene (177698-19-0,25719-60-2) + Pinene (80-56-8,177698-18-9,25766-18-1) + sabinene (2009-00-9,10408-16-9,15826-80-9,3387-41-5) + beta-phellandrene (555-10-2) + (-)-(S)-limonene (5989-54-8,555-08-8,8022-90-0,9003-73-0,95327-98-3)

Guidance literature:

With Mentha spicata S-limonene synthase, (N₃₄₅A/L₄₂₃A/S₄₅₄G) mutant; magnesium chloride; D,L-dithiothreitol; In hexane; glycerol; at 37 ℃; for 0.666667h; pH=7; chemoselective reaction; Mechanism; Enzymatic reaction;

DOI:10.1016/j.phytochem.2017.02.017

Reference yield:

geranyl diphosphate (763-10-0) → sabinene (2009-00-9,10408-16-9,15826-80-9,3387-41-5) + (-)-(S)-limonene (5989-54-8,555-08-8,8022-90-0,9003-73-0,95327-98-3)

Guidance literature:

With Mentha spicata S-limonene synthase, mutant (C₃₂₁Y/N₃₄₅A/L₄₂₃A/S₄₅₄A); magnesium chloride; D,L-dithiothreitol; In hexane; glycerol; at 37 ℃; for 0.666667h; pH=7; chemoselective reaction; Mechanism; Enzymatic reaction;

DOI:10.1016/j.phytochem.2017.02.017

upstream raw materials:

geranyl diphosphate

1-chloro-3,7-dimethylocta-2,6-diene

Downstream raw materials:

formic acid p-menth-1-en-4-yl ester

1,4-dibromo-p-menthane

1-methyl-4-isopropyl-1,3-cyclohexadiene

1,4-dichloro-p-menthane

Refernces

• 1、 Gatto, Nathalie,Vattekkatte, Abith,K?llner, Tobias,Degenhardt, J?rg,Gershenzon, Jonathan,Boland, Wilhelm. "Isotope sensitive branching and kinetic isotope effects to analyse multiproduct terpenoid synthases from Zea mays". . p. 3797 - 3800. Retrieved 2015/03/30.
• 2、 Fischbach, Robert J.,Zimmer, Ina,Steinbrecher, Rainer,Pfichner, Andreas,Schnitzler, Joerg-Peter. "Monoterpene synthase activities in leaves of Picea abies (L.) Karst. and Quercus ilex L.". . p. 257 - 265. Retrieved 2007/10/03.