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CAS Number: 124-76-5
EC Number: 204-712-4
Molecular Weight: 154.25
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–Ponndorf–Verley 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, 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 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 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.
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.
For isoborneol (USEPA/OPP Pesticide Code: 047089) there are 0 labels match.
Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses.
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 of Isoborneol:
Fragrance Ingredients
Odor agents
Consumer Uses of Isoborneol:
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
Therapeutic Uses of Isoborneol:
Isoborneol, a monoterpene and a component of several plant essential oils, has shown dual virucidal activity against herpes simplex virus 1 (HSV-1).
First, Isoborneol inactivated HSV-1 by almost 4 log10 within 30 minutes of exposure, and second, at a concentration of 0.06%, isoborneol completely inhibited viral replication without affecting viral adsorption.
Isoborneol did not exhibit significant cytotoxicity at concentrations ranging from 0.016% to 0.08% when tested against human and monkey cell lines.
Isoborneol specifically inhibited the glycosylation of viral polypeptides based on the following data: fully glycosylated mature forms of the two viral glycoproteins gB and gD were not detected when the virus was replicated in the presence of isoborneol, no major changes in the cellular glycosylation pattern were observed.
Polypeptides between untreated and isoborneol-treated Vero cells, isoborneol did not affect the glycosylation of gB produced from one copy of the gB gene located in the cellular genome, and other monoterpenes such as 1,8-cineol and borneol, a stereoisomer of isoborneol, do not inhibit HSV-1 glycosylation.
Use Classification of Isoborneol:
Food additives - Flavoring Agents
Flavouring Agent - FLAVOURING_AGENT; - JECFA Functional Classes
Flavoring Agents - JECFA Flavorings Index
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.
Methods of Manufacturing 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 of Isoborneol:
All other chemical product and preparation manufacturing
Plastic 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.
Solubility of Isoborneol:
Insoluble in water.
Soluble in dipropylene glycol, ethyl alcohol (1gm. in 2ml. 70% alcohol).
Fire Fighting Procedures 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.
Firefighting Hazards of Isoborneol:
Special hazards arising from Isoborneol or mixture: Carbon oxides
Cleanup Methods 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 product 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 the material for Isoborneol approved use or return Isoborneol to the manufacturer or supplier.
Ultimate disposal of the chemical must consider: the material'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 this material is highly flammable.
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging: Dispose of as unused product.
Preventive Measures of Isoborneol:
Avoid contact with skin and eyes.
Avoid formation of dust and aerosols.
Further processing of solid materials may result in the formation of combustible dusts.
The potential for combustible dust formation should be taken into consideration before additional processing occurs.
Provide appropriate exhaust ventilation at places where dust is formed.
Keep away from sources of ignition - No smoking.
Take measures to prevent the build up of electrostatic charge.
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 product enter drains.
Gloves must be inspected prior to use.
Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with Isoborneol.
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.
Storage Conditions of Isoborneol:
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
Properties of Isoborneol:
Molecular Weight: 154.25
XLogP3: 2.7
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 1
Rotatable Bond Count: 0
Exact Mass: 154.135765193
Monoisotopic Mass: 154.135765193
Topological Polar Surface Area: 20.2 Ų
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
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
Physical Properties of Isoborneol:
Appearance: white crystalline solid (est)
Assay: 92.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 213.00 °C. @ 760.00 mm Hg
Boiling Point: 212.00 °C. @ 760.00 mm Hg (est)
Vapor Pressure: 0.040000 mmHg @ 25.00 °C. (est)
Flash Point: 200.00 °F. TCC ( 93.33 °C. )
logP (o/w): 3.240
Shelf Life: 36.00 month(s) or longer if stored properly.
Storage: store in cool, dry place in tightly sealed containers, protected from heat and light.
Soluble in: dipropylene glycol - ethyl alcohol, 1gm. in 2ml. 70% alcohol - water, 1186 mg/L @ 25 °C (est)
Insoluble in: water
Stability: non-discoloring in most media
Specifications of Isoborneol:
Melting Point: ∼210°C (sublimation)
Flash Point: 74°C (165°F)
Odor: Strong
UN Number: UN1325
Beilstein: 4126091
Merck Index: 14,5128
Quantity: 25g
Formula Weight: 154.25
Percent Purity: 95%
Chemical Name or Material: (±)-Isoborneol
Synonyms of Isoborneol:
Isoborneol
Exoborneol
DL-Isoborneol
Isobornyl alcohol
exo-2-Camphanol
exo-2-Bornanol
NSC26350
Isoborneol, DL-
124-76-5
SCHEMBL56715
NSC-26350
AKOS015913967
ZINC100046351
exo-2-Hydroxy-1,7-trimethylnorbornane
exo-1,7-Trimethylbicyclo[2.2.1]heptan-2-ol
Bicyclo[2.2.1]heptan-2-ol,7,7-trimethyl-, exo-
UNII-L88RA8N5EG component DTGKSKDOIYIVQL-KHQFGBGNSA-N
(-)-Isoborneol
(1R,2R,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol
(1R,2R,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol
(1R,2R,4R)-1,7,7-Triméthylbicyclo[2.2.1]heptan-2-ol
10334-13-1
124-76-5
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)-
exo-2-Borneol
exo-borneol
ISOBORNEOL
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
10385-78-1
507-70-0
874571-72-9
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
missing
rac-(1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
