ISOBORNEOL

Isoborneol, also known as borneol, belongs to the class of organic compounds known as bicyclic monoterpenoids.

Isoborneol is a monoterpenoid alcohol present in the essential oils of numerous medicinal plants and has antioxidant and antiviral properties.

Isoborneol is used as a synthetic flavor, as a moth repellent, cold sore topical medication, muscle liniment, and steam-inhaled cough suppressant.

CAS Number: 124-76-5

EC Number: 204-712-4

Molecular Formula: C10H18O

Molecular Weight (g/mol): 154.253

Synonyms:, Isoborneol, (-)-Isoborneol, 124-76-5, DL-Isoborneol, Isocamphol, L-Isoborneol, Isobornyl alcohol, (-)-(2R)-Isoborneol, Isoborneol, (-)-, 2-exo-Bornyl alcohol, 10334-13-1, Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, (1R,2R,4R)-rel-, (-)-Bornan-2-exo-ol, FEMA No. 2158, (1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol, Isoborneol (1R,2R,4R)-form [MI], L88RA8N5EG, Exoborneol, DTXSID2042060, exo-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol, NSC 26350, 20U67Z994U, exo-2-Hydroxy-1,7,7-trimethylnorbornane, Bicyclo(2.2.1)heptan-2-ol, 1,7,7-trimethyl-, (1R,2R,4R)-, (1R,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2alpha-ol, Isoborneol, DL-, Isobomeol, Bicyclo(2.2.1)heptan-2-ol, 1,7,7-trimethyl-, (1R,2R,4R)-rel-, 2-Bornanol, exo-, 2-Camphanol, exo-, exo-1,7,7-Trimethylbicyclo(2.2.1)heptan-2-ol, 507-70-0, UNII-L88RA8N5EG, Bicyclo(2.2.1)heptan-2-ol, 1,7,7-trimethyl-, exo-, b-Camphol, NSC-26350, UNII-20U67Z994U, HSDB 2843, EINECS 204-712-4, Isoborneol, 95%, BRN 4126091, ISOBORNEOL,DL-, ISOBORNEOL [MI], AI3-14113, ISOBORNEOL [FCC], ISOBORNEOL [FHFI], ISOBORNEOL [HSDB], Isoborneol, >=95%, FG, SCHEMBL115722, 1,7,7-Trimethylbicyclo(2.2.1)heptan-2-ol, exo-, Isoborneol, analytical standard, ISOBORNEOL,(+/-)-, CHEMBL3560760, DTXCID0022060, FEMA 2158?, HY-N2004, Tox21_301645, MFCD00074821, AKOS028109482, NCGC00255879-01, BS-43851, CAS-124-76-5, CS-0018324, EN300-179986, EN300-760916, A828291, J-005169, Q15644616, (1R,3R,4R)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanol, (1R,3R,4R)-4,7,7-trimethylbicyclo[2.2.1]heptan-3-ol, rac-(1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol, rel-(1R,2R,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol, (1R*,2R*,4R*)-1,7,7-Trimethyl-bicyclo[2.2.1]heptan-2-ol, (-)-Isoborneol, (1R,2R,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol [ACD/IUPAC Name], (1R,2R,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol [German] [ACD/IUPAC Name], (1R,2R,4R)-1,7,7-Triméthylbicyclo[2.2.1]heptan-2-ol [French] [ACD/IUPAC Name], 10334-13-1 [RN], 124-76-5 [RN], Bicyclo(2.2.1)heptan-2-ol, 1,7,7-trimethyl-, (1R,2R,4R)-rel-, Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, (1R,2R,4R)- [ACD/Index Name], exo-2-Borneol, exo-borneol, ISOBORNEOL [Wiki], ISOBORNEOL, (-)-, (+)-Isoborneol, (1R,2R,4R)-1,7,7-trimethyl-2-norbornanol, (1R,2R,4R)-1,7,7-trimethylnorbornan-2-ol, (1R,2R,4R)-Isoborneol, (1R,2R,4R)-rel-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-ol, (1R,3R,4R)-4,7,7-trimethylbicyclo[2.2.1]heptan-3-ol, (1R,4R,6R)-1,7,7-trimethylbicyclo[2.2.1]heptan-6-ol, 1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol [ACD/IUPAC Name], 10385-78-1 [RN], 507-70-0 [RN], 874571-72-9 [RN], b-Camphol, Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, (1R,2R,4R)-rel-, Bicyclo[2.2.1]heptan-2-ol,1,7,7-trimethyl-, (1R,2R,4R)-rel-, exo-1,7,7-trimethylbicyclo(2.2.1)-2-heptanol, exo-1,7,7-Trimethylbicyclo(2.2.1)heptan-2-ol, exo-2-Bornanol, exo-2-Camphanol, iso-Camphol, Isocamphol, MFCD18086994 [MDL number], missing, rac-(1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol

Isoborneol is a bicyclic organic compound and a terpene derivative.

The hydroxyl group in this compound is placed in an exo position.

The endo diastereomer is called borneol.

Being chiral, isoborneol exists as enantiomers.

Isoborneol ((±)-Isoborneol) is a monoterpenoid alcohol present in the essential oils of numerous medicinal plants and has antioxidant and antiviral properties.

Isoborneol is a potent inhibitor of herpes simplex virus type 1 (HSV-1)

Isoborneol, also known as borneol, belongs to the class of organic compounds known as bicyclic monoterpenoids.

These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units.

The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids.

Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes.

GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements.

Borneol can be synthesized by reducing camphor by the Meerwein‚ ÄìPonndorf‚ ÄìVerley reaction, a reversible, inexpensive process.

The isomer isoborneol can be produced in the kinetically controlled reduction of camphor with sodium borohydride, which is fast and irreversible.

(-)-Isoborneol is neutral compound, a white crystalline solid with a balsamic camphoreous herbal woody odor and camphoreous minty herbal earthy woody flavor.

Borneol or isoborneol is a naturally occurring organic compound found in the essential oil of many plants such as camphorweed, mugwort, beautyberry, Ngai camphor, aromatic ginger.

Isoborneol is used as a synthetic flavor, as a moth repellent, cold sore topical medication, muscle liniment, and steam-inhaled cough suppressant.

Isoborneol is also used in Used in perfumes.

Isoborneol, also known as isobornyl alcohol, belongs to the class of organic compounds known as bicyclic monoterpenoids.

These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Based on a literature review a small amount of articles have been published on Isoborneol.

Isoborneol is a terpene derivative.

Isoborneol is prepared by hydration and rearrangement of camphene/pinene.

Isoborneol is commonly used as flavor and fragrance agents

Applications of Isoborneol:

Isoborneol is used in fragrance formulation of daily chemicals

Isoborneol is used in daliy and industrial flavor

Isoborneol is used in producing rosemary and lavandula angustifolia

Isoborneol is used as antiseptics.

Isoborneol is used as a synthetic flavor, as a moth repellent, cold sore topical medication, muscle liniment, and steam-inhaled cough suppressant.

Isoborneol is also used in Used in perfumes.

Uses of Isoborneol:

Isoborneol is used as a synthetic flavor.

In over-the-counter preparations containing <11% camphor, Isoborneol has been used as a moth repellent, cold sore topical medication, muscle liniment, and steam-inhaled cough suppressant. Isoborneol is used in perfumes. The repellence of the plant-derived bicyclic monoterpenoid isoborneol on subterranean termites was assessed in short-term laboratory bioassays. Depending on concentration, application of isoborneol to different soil types was efficient in creating repellent soil barriers, which were not penetrated by workers of Reticulitermes santonensis De Feytaud or R. flavipes Kollar within 2 wk after adding Isoborneol to the substrate. Isoborneol-treated barriers did not affect termite survival. The bioavailability of the active ingredient decreased with increasing clay content of the soil. Evaporation of isoborneol from treated soil increased with increasing particle size of the substrate and could be reduced by covering the soil surface. Industry Uses: Fragrance Ingredients Odor agents Odor agents Other (specify) Consumer Uses: Air care products Cleaning and furnishing care products Laundry and dishwashing products Non-TSCA use Personal care products Plastic and rubber products not covered elsewhere Fragrance Odor agents Solubility of Isoborneol: Insoluble in water. Soluble in dipropylene glycol, ethyl alcohol (1gm. in 2ml. 70% alcohol). Preparation of Isoborneol: Isoborneol is synthesized commercially by hydrolysis of isobornyl acetate. The latter is obtained from treatment of camphene with acetic acid in the presence of a strong acid catalyst. Isoborneol can also be produced by reduction of camphor. Isoborneol derivatives as chiral ligands: Derivatives of isoborneol are used as ligands in asymmetric synthesis. (2S)-(−)-3-exo-(morpholino)isoborneol or MIB with a morpholine substituent in the α-hydroxyl position. (2S)-(−)-3-exo-(dimethylamino)isoborneol or DAI with a dimethylamino substituent in the α-hydroxyl position Absorption, Distribution and Excretion of Isoborneol: The percutaneous absorptions of camphene, isoborneol-acetate, limonene, menthol and alpha-pinene as constituents of a foam bath (Pinimenthol) were measured on animals using radioactively labeled ingredients. Pharmacokinetic measurements showed maximum blood levels for all tested ingredients 10 min after the onset of percutaneous absorption. None of the ingredients was preferentially absorbed. Blood levels of all ingredients after 10 min of percutaneous absorption were a direct function of the size of the skin area involved. Manufacturing Methods of Isoborneol: By hydrolysis of isobornyl acetate, or by catalytic reduction of camphor (both d- and l-isomers); the optically inactive compound can be prepared by treating camphene with 1:1 mixture of sulfuric acid and glacial acetic acid and then hydrolyzing the isobornyl acetate. General Manufacturing Information of Isoborneol: Industry Processing Sectors: All Other Chemical Product and Preparation Manufacturing Plastics Material and Resin Manufacturing Soap, Cleaning Compound, and Toilet Preparation Manufacturing Analytic Laboratory Methods of Isoborneol: Method: USGS-NWQL O-1433-01; Procedure: gas chromatography/mass spectrometry. Analyte: isoborneol. Matrix: filtered wastewater and natural-water samples. Detection Limit: 0.11 ug/L. Method: USGS-NWQL O-4433-06. Procedure: continuous liquid-liquid extractor with gas chromatography with mass spectrometry detection. Analyte: isoborneol. Matrix: whole wastewater and environmental water samples. Detection Limit: 0.05 ug/L. Gas chromatography (GC)-NMR method is described for detecting isoborneol in commercial borneol preparations. Isoborneol detected by chromatographic analysis with previous absorption. Determination was made by internal reference method with naphthalene as reference. Resolution of chiral compounds has played an important role in the pharmaceutical field, involving detailed studies of pharmacokinetics, physiological, toxicological, and metabolic activities of enantiomers. Herein, a reliable method by high-performance liquid chromatography (HPLC) coupled with an optical rotation detector was developed to separate isoborneol enantiomers. A cellulose tris(3, 5-dimethylphenylcarbamate)-coated chiral stationary phase showed the best separation performance for isoborneol enantiomers in the normal phase among four polysaccharide chiral packings. The effects of alcoholic modifiers and column temperature were studied in detail. Resolution of the isoborneol racemate displayed a downward trend along with an increase in the content of ethanol and column temperature, indicating that less ethanol in the mobile phase and lower temperature were favorable to this process. Moreover, two isoborneol enantiomers were obtained via a semipreparative chiral HPLC technique under optimum conditions, and further characterized by analytical HPLC, and experimental and calculated vibrational circular dichroism (VCD) spectroscopy, respectively. The solution VCD spectrum of the first-eluted component was consistent with the Density Functional Theory (DFT) calculated pattern based on the SSS configuration, indicating that this enantiomer should be (1S, 2S, 4S)-(+)-isoborneol. Briefly, these results have provided reliable information to establish a method for analysis, preparative separation, and absolute configuration of chiral compounds without typical chromophoric groups. Handling and Storage of Isoborneol: Storage Conditions: Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place. Storage of Isoborneol: Avoid contact with light Keep separated from incompatible substances Store and handle in accordance with all current regulations and standards Store in a cool, dry place Store in a tightly closed container Fire Fighting of Isoborneol: Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary. Further information: Use water spray to cool unopened containers. Accidental Release Measures of Isoborneol: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let Isoborneol enter drains. Methods and materials for containment and cleaning up: Sweep up and shovel. Contain spillage, and then collect with an electrically protected vacuum cleaner or by wetbrushing and place in container for disposal according to local regulations. Keep in suitable, closed containers for disposal. Contain spillage, pick up with an electrically protected vacuum cleaner or by wet-brushing and transfer to a container for disposal according to local regulations. Disposal Methods of Isoborneol: Recycle any unused portion of Isoborneol for its approved use or return Isoborneol to the manufacturer or supplier. Ultimate disposal of the chemical must consider: Isoborneol's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If Isoborneol is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as Isoborneol is highly flammable. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of Isoborneol. Contaminated packaging: Dispose of as unused Isoborneol. Identifiers of Isoborneol: CAS Number: +: 16725-71-6 d -: 10334-13-1 rac: 124-76-5 ChEBI +: CHEBI:191949 ChEMBL: +: ChEMBL4294644 -: ChEMBL3560760 ChemSpider: +: 16739225 -: 4882019 PubChem CID: +: 6973640 -: 6321405 UNII: +: 8GDX32M6KF -: 20U67Z994U rac: L88RA8N5EG UN number: 1312 InChI +: InChI=1S/C10H18O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m0/s1 Key: DTGKSKDOIYIVQL-OYNCUSHFSA-N Key -: InChI=1S/C10H18O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m1/s1 Key: DTGKSKDOIYIVQL-MRTMQBJTSA-N SMILES: +: C[C@]12CC[C@H](C1(C)C)C[C@@H]2O -: C[C@@]12CC[C@@H](C1(C)C)C[C@H]2O rac: CC1(C2CCC1(C(C2)O)C)C Empirical Formula (Hill Notation): C10H18O CAS Number: 124-76-5 Molecular Weight: 154.25 EC Number: 204-712-4 MDL number: MFCD00074821 PubChem Substance ID: 24895930 NACRES: NA.22 CAS: 124-76-5 Molecular Formula: C10H18O Molecular Weight (g/mol): 154.253 MDL Number: MFCD00074821 InChI Key: DTGKSKDOIYIVQL-SZBHIRRCSA-N Synonym: dl-isoborneol PubChem CID: 126961757 IUPAC Name: (1R,3R)-4,7,7-trimethylbicyclo[2.2.1]heptan-3-ol SMILES: CC1(C2CCC1(C(C2)O)C)C Properties of Isoborneol: Chemical formula: C10H18O Molar mass: 154.253 g·mol−1 Appearance: white or colorless solid Melting point: 212–214 °C (414–417 °F; 485–487 K) + or -; 210–215 °C for rac Quality Level: 100 Assay: 95% mp: 212-214 °C (subl.) (lit.) SMILES string: [H][C@@]12CC[C@@](C)([C@H](O)C1)C2(C)C InChI: 1S/C10H18O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m1/s1 InChI key: DTGKSKDOIYIVQL-MRTMQBJTSA-N Formula: C10H18O Purity: >70.0%(GC)

Color/Form: White to Almost white powder to crystal

InChI: InChI=1S/C10H18O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7-8,11H,4-6H2,1-3H3

InChI key: InChIKey=DTGKSKDOIYIVQL-UHFFFAOYSA-N

SMILES: CC1(C)C2CCC1(C)C(O)C2

MDL: MFCD00066426

Melting point: 201 °C

Flash point: 201 °C

HS code: 2906190090

Molecular Weight: 154.25 g/mol

XLogP3: 2.7

Hydrogen Bond Donor Count: 1

Hydrogen Bond Acceptor Count: 1

Rotatable Bond Count: 0

Exact Mass: 154.135765193 g/mol

Monoisotopic Mass: 154.135765193 g/mol

Topological Polar Surface Area: 20.2Ų

Heavy Atom Count: 11

Complexity: 185

Isotope Atom Count: 0

Defined Atom Stereocenter Count: 3

Undefined Atom Stereocenter Count: 0

Defined Bond Stereocenter Count: 0

Undefined Bond Stereocenter Count: 0

Covalently-Bonded Unit Count: 1

Compound Is Canonicalized: Yes

Specifications of Isoborneol:

Melting Point: ∼210°C (sublimation)

Flash Point: 74°C (165°F)

Odor: Strong

Quantity: 25 g

UN Number: UN1325

Beilstein: 4126091

Merck Index: 14,5128

Formula Weight: 154.25

Percent Purity: 95%

Chemical Name or Material: (±)-Isoborneol

Names of Isoborneol:

IUPAC name:

(1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptane-2-ol, (1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2-ol