L(-)-Borneol

Base Information

• Chemical Name: L(-)-Borneol
• CAS No.: 464-45-9
• Deprecated CAS: 95650-45-6,1140588-66-4,2350248-19-8
• Molecular Formula: C10H18 O
• Molecular Weight: 154.252
• Hs Code.: 29061900
• European Community (EC) Number: 207-353-1,208-080-0
• UN Number: 1312
• UNII: 1Y84986J9Q
• DSSTox Substance ID: DTXSID3022035
• Nikkaji Number: J9.306H
• Wikipedia: Borneol
• Wikidata: Q27089413
• RXCUI: 1368202
• Metabolomics Workbench ID: 46785
• ChEMBL ID: CHEMBL3186705
• Mol file: 464-45-9.mol

Synonyms:Bicyclo[2.2.1]heptan-2-ol,1,7,7-trimethyl-, (1S-endo)-; Borneol, (1S,2R,4S)-(-)- (8CI); (-)-(1S,4S)-Borneol;(-)-Borneol; (-)-[(1S)-endo]-Borneol; (-)-endo-Borneol; (1S)-(-)-Borneol;(1S)-endo-(-)-Borneol; (1S)-endo-Borneol; (1S,2R,4S)-Borneol;(1S-endo)1,7,7-Trimethyl-bicyclo[2.2.1]heptan-2-ol; (2R)-(-)-Borneol;L-Borneol; Linderol; Ngai camphor; endo-(-)-Borneol; endo-(1S)-(-)-Borneol;l-Borneol

Chemical Property of L(-)-Borneol

Chemical Property:

• Appearance/Colour: White powder or chunks
• Vapor Pressure: 33.5 mm Hg ( 25 °C)
• Melting Point: 204-208 ºC
• Refractive Index: -36 ° (C=5, EtOH)
• Boiling Point: 210 ºC
• PKA: 15.36±0.60(Predicted)
• Flash Point: 65 ºC
• PSA: 20.23000
• Density: 0.992g/cm³
• LogP: 2.19350
• Storage Temp.: Flammables area
• Solubility.: almost transparency in EtOH
• Water Solubility.: INSOLUBLE
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 154.135765193
• Heavy Atom Count: 11
• Complexity: 185
• Transport DOT Label: Flammable Solid

Purity/Quality:

99% ^*data from raw suppliers

(-)-Borneol ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F,Xi
• Statements: 11-43
• Safety Statements: 16-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Alcohols and Polyols, Other,Biological Agents -> Plant Oils and Extracts
• Canonical SMILES: CC1(C2CCC1(C(C2)O)C)C
• Isomeric SMILES: C[C@]12CC[C@H](C1(C)C)C[C@H]2O
• Description: Borneol is an analgetic, antibacterial, and resuscitation-inducing norborneol derived from fresh branches and leaves of Cinnamomum camphora (L.) Presl. Far more than 2000?years ago, it has been introduced to China . In China, it has been firstly recorded in Ming Yi Bie Lu and then included in Tang Ben Cao. It was recorded in history that borneol was derived from Dryobalanops camphora gaertner and then precipitated from the resin to form the natural crystal compound or distilled from the trunk and cooled down to form the crystal compound, which is certified from Indonesia. In China, the natural borneol mainly relied on imports. In recent years, it was extracted from the Lauraceae plants, including Cinnamomum camphora, Cinnamomum longepaniculatum, and Cinnamomum burmannii, which greatlyincreases the resources of natural borneol for China. Cinnamomum camphora is mainly distributed in Jiangxi and Fujian provinces with 81.78% of borneol. Cinnamomum longepaniculatum is mainly distributed in Hunan and Sichuan provinces with 77.57% of borneol. Cinnamomum burmannii is mainly distributed in Yunnan and Guangxi provinces with 70.81% of borneol. Among them, Cinnamomum camphora contains more borneol than the other two types .
• Physical properties: Appearance: colorless to white lumps. Odor: pungent, camphor-like. Density:1.011?g/ cm3 (20?°C). Melting point: 208?°C (406?°F; 481?K). Boiling point: 213?°C (415?°F; 486?K). Solubility: slightly soluble in water (D-form), soluble in chloroform, ethanol, acetone, ether, benzene, toluene, decalin, and tetralin. Flash point: 65? °C (149?°F; 338?K). It’s stable under sealed condition while volatile in the air.
• Uses: (-)-Borneol is used to prepare its esters by reacting with acids. Its derivatives are used as chiral ligands in asymmetric synthesis. It is also used in flavors and perfumes. Further, it is used in traditional Chinese medicine as moxa. In addition to this, it is used as a component of many essential oils and also used as a natural insect repellent. (-)-Borneol has been used to study its antiapoptotic, antioxidative and neuroprotective effect in human neuroblastoma cells (SH-SY5Y).
• Indications: The main efficacy of borneol is to induce resuscitation (with aromatic stimulation), clear stagnated fire (fever feeling), remove nebula for improving eyesight, and relieve swelling and pain. The indications of borneol are sore throat, aphthous, red eyes, purulent ear discharge, convulsions, febrile delirium, sudden faint due to qi depression, stroke, and coma. In Chinese traditional medicine, the borneol is often used as an envoy drug and combined with other drugs but is not used as a single medicine with the inexact efficacy
• Clinical Use: As a traditional Chinese medicine, borneol is commonly used as envoy drugs in the compatibility of traditional Chinese medicine. On behalf of combination drugs such as Danshen dripping pills, Niu Huang Jie Du pills, and watermelon cream, its effect is significant because of its special aromatic smell. Borneol with a certain irritation, oral administration may cause the gastrointestinal discomforts, severely causes vomiting and other adverse reactions.

Technology Process of L(-)-Borneol

There total 147 articles about L(-)-Borneol 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: 97.0%

isobornyl acetate (28974-17-6) → isoborneol (124-76-5,464-43-7,464-45-9,507-70-0,6627-72-1,10334-13-1,10385-78-1,16725-71-6,24393-70-2)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; for 168h; Ambient temperature;

Reference yield: 96.0%

Carbonic acid 1-(3,5-dimethoxy-phenyl)-2-oxo-2-phenyl-ethyl ester (1R,2R,4R)-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester → isoborneol (124-76-5,464-43-7,464-45-9,507-70-0,6627-72-1,10334-13-1,10385-78-1,16725-71-6,24393-70-2)

Guidance literature:

In benzene; for 1h; Irradiation;

DOI:10.1021/jo00110a011

Reference yield: 90.0%

(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (464-49-3,68546-28-1) → isoborneol (124-76-5,464-43-7,464-45-9,507-70-0,6627-72-1,10334-13-1,10385-78-1,16725-71-6,24393-70-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -78 - 25 ℃; for 22h;

DOI:10.1002/anie.202110849

upstream raw materials:

tetrachloromethane

phthalic anhydride

ethanol

beta-pinene

Downstream raw materials:

rac-endo-borneol

(4-phenylazo-phenyl)-carbamic acid-((1S)-bornyl ester)

(1S,3R)-(-)-camphoric acid

(1S)-camphor

Refernces

• 1、 Badji?, Jovica D.,Finnegan, Tyler J.,Gunther, Michael J.,Pavlovi?, Radoslav Z.,Wang, Xiuze. "Enantioselective Construction of Modular and Asymmetric Baskets". supporting information. p. 25075 - 25081. Retrieved 2021/10/25.
• 2、 Drienovská, Ivana,Kolanovi?, Dajana,Chánique, Andrea,Sieber, Volker,Hofer, Michael,Kourist, Robert. "Molecular cloning and functional characterization of a two highly stereoselective borneol dehydrogenases from Salvia officinalis L". . . Retrieved 2020/01/11.