(+)-Isoborneol

Base Information

• Chemical Name: (+)-Isoborneol
• CAS No.: 124-76-5
• Molecular Formula: C10H18O
• Molecular Weight: 154.252
• Hs Code.: 2906.19 Oral ratLD50: 5033 mg/kg
• European Community (EC) Number: 204-712-4,208-080-0
• UN Number: 1312
• UNII: 8GDX32M6KF
• DSSTox Substance ID: DTXSID40168259
• Nikkaji Number: J150.348K
• Wikipedia: Isoborneol
• Wikidata: Q27270411
• Metabolomics Workbench ID: 47073
• ChEMBL ID: CHEMBL4294644
• Mol file: 124-76-5.mol

Synonyms:(+)-Isoborneol;Isoborneol, (+)-;(S,S,S)-(+)-Isoborneol;16725-71-6;UNII-8GDX32M6KF;8GDX32M6KF;Isoborneol, (1S,2S,4S)-(+)-;Isoborneol (1S,2S,4S)-form [MI];Bicyclo(2.2.1)heptan-2-ol, 1,7,7-trimethyl-, (1S,2S,4S)-;(1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol;Isoborneol;1-Bornyl alcohol;(1S,4beta)-1alpha,7,7-Trimethylbicyclo[2.2.1]heptane-2beta-ol;epi-Borneol;Borneol, (1S,2R,4S)-(-)-;(?)-borneol;(1S - endo) - 1,7,7 - trimethylbicyclo(2.2.1)heptan - 2 - ol;SCHEMBL2469360;CHEMBL4294644;FEMA 2158;DTXSID40168259;CHEBI:191949;DTGKSKDOIYIVQL-OYNCUSHFSA-N;124-76-5;507-70-0;AKOS037643879;AS-39230;Q27270411;Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, (1S-exo)-

Chemical Property of (+)-Isoborneol

Chemical Property:

• Appearance/Colour: white to almost white crystalline powder
• Vapor Pressure: 0.0398mmHg at 25°C
• Melting Point: 212-214 °C (subl.)(lit.)
• Refractive Index: 1.502
• Boiling Point: 212 °C at 760 mmHg
• PKA: 15.36±0.60(Predicted)
• Flash Point: 65.6 °C
• PSA: 20.23000
• Density: 0.992 g/cm³
• LogP: 2.19350
• Storage Temp.: 2-8°C
• Solubility.: almost transparency in Methanol
• 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:

99.9% ^*data from raw suppliers

DL-Isoborneol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F, Xi
• Hazard Codes: F,Xi
• Statements: 11-38
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Alcohols and Polyols, Other
• Canonical SMILES: CC1(C2CCC1(C(C2)O)C)C
• Isomeric SMILES: C[C@]12CC[C@H](C1(C)C)C[C@@H]2O
• Description: Isoborneol has a piney, camphoraceous odor. May be prepared by the hydrolysis of isobomyl acetate, or by catalytic reduction of camphor (both d- and ι-isomers); the optically inactive compound can be prepared by treating camphene with a 1:1 mixture of sulfuric acid and glacial acetic acid and then hydrolyzing the isobomyl acetat.
• Uses: Used as a synthetic flavor, as a moth repellent, cold sore topical medication, muscle liniment, and steam-inhaled cough suppressant. It is also used in Used in perfumes. Isoborneol is a monoterpene and a component of several plant essential oils, showed dual viricidal activity against herpes simplex virus 1 (HSV-1).

Technology Process of (+)-Isoborneol

There total 75 articles about (+)-Isoborneol 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:

(1S)-camphor

isoborneol

Camphor

isobornyl butyrate

Downstream raw materials:

diphenylbornyl phosphite

2-methoxy-4-methylthiobenzoic acid bornyl ester

(1S)-camphor

(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

Refernces

• 1、 Calderini, Elia,Drienovská, Ivana,Myrtollari, Kamela,Pressnig, Michaela,Sieber, Volker,Schwab, Helmut,Hofer, Michael,Kourist, Robert. "Simple Plug-In Synthetic Step for the Synthesis of (?)-Camphor from Renewable Starting Materials". . p. 2951 - 2956. Retrieved 2021/06/18.
• 2、 Baev, Dmitriy S.,Maksyutov, Rinat A.,Mordvinova, Ekaterina D.,Pyankov, Oleg V.,Salakhutdinov, Nariman F.,Shcherbakov, Dmitriy N.,Shcherbakova, Nadezhda S.,Sokolova, Anastasiya S.,Tolstikova, Tatyana G.,Yarovaya, Olga I.,Zaykovskaya, Anna V.,Zybkina, Anastasiya V.. "Monoterpenoid-based inhibitors of filoviruses targeting the glycoprotein-mediated entry process". . . Retrieved 2020/09/09.