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Home > Encyclopedia > endo-Borneol

endo-Borneol

pharmaceutical raw materials
endo-Borneol structure

endo-Borneol 

structure
  • CAS No:

    507-70-0

  • Formula:

    C10H18O

  • Chemical Name:

    endo-Borneol

  • Synonyms:

    Bicyclo[2.2.1]heptan-2-ol,1,7,7-trimethyl-,(1R,2S,4R)-rel-;Borneol;Bicyclo[2.2.1]heptan-2-ol,1,7,7-trimethyl-,endo-;rel-(1R,2S,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol;Camphol;endo-Borneol;endo-2-Hydroxy-1,7,7-trimethylnorbornane;2-Borneol;2-endo-Bornyl alcohol;dl-Borneol;(±)-Borneol;endo-(±)-Bornan-2-ol;NSC 60223;rel-(1S,2R,4S)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol;6627-72-1;778604-05-0;880145-24-4

  • Categories:

    Cosmetic Ingredient  >  Perfuming

Description

solid Borneol is a bicyclic terpene alcohol. Borneol is an endo isomer; the corresponding exo isomer is isoborneol:
Borneol occurs abundantly in nature as a single enantiomer or, less frequently, as the racemate. (1S,2R,4S)-(?)-Borneol occurs particularly in oils from Pinaceae species and in citronella oil. (1R,2S,4R)-(+)-Borneol is found, for example, in camphor oil (Ho-Sho oil), rosemary, lavender, and olibanum oils. Borneol is a colorless, crystalline solid. (+)-Borneol has a camphorace


Borneol appears as a white colored lump-solid with a sharp camphor-like odor. Burns readily. Slightly denser than water and insoluble in water. Used to make perfumes.|Liquid|White to off-white crystals; piney camphoraceous aroma


Borneol appears as a white colored lump-solid with a sharp camphor-like odor. Burns readily. Slightly denser than water and insoluble in water. Used to make perfumes.

endo-Borneol Basic Attributes

154.25

154.25

207-353-1

60223|26352

1312

DTXSID3052143

White to off-white crystals|White translucent lumps

29061990

Characteristics

20.2

log Kow = 2.69

Borneol appears as a white colored lump-solid with a sharp camphor-like odor. Burns readily. Slightly denser than water and insoluble in water. Used to make perfumes.

0.9864 g/cm3 @ Temp: 20 °C

204 °C

213.2 °C

150 °F

1.532

H2O: insoluble

33.5 mm Hg ( 25 °C)

5.31 (vs air)

Piney, camphor-like odor

Burning taste somewhat reminiscent of mint

Henry's Law constant = 1.38E-05 atm-cu m/mol at 25 °C (est)

Leaves or hexagonal plates from petroleum ether /D-Borneol/|Peculiar peppery odor and burning taste somewhat resembling that of mint; melting point: 208 °C; density: 1.011 at 20 °C/4 °C; boiling point: 212 °C /D-Borneol/|Soluble in alcohol, benzene, toluene, acetone, decalin, tetralin. /D-Borneol/|Sublimes, but is less volatile than camphor /D-Borneol/|log Kow = 3.01 /L-Borneol/|log Kow = 3.24 /Isoborneol/|Hydroxyl radical reaction rate constant = 1.14X10-11 cu cm/molec-sec at 25 °C

Flammable. Insoluble in water.

Alcohols and Polyols

BORNEOL is an alcohol. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.

Safety Information

III

4.1

UN 1312 4.1/PG 3

2

11-43-22

16-36/37

DT5095000

F,Xi,Xn

Stable. Highly flammable. Incompatible with strong oxidizing agents.

SRP: Recycle any unused portion of the material for its approved use or return it 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 it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

Borneol is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and b) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

Excerpt from ERG Guide 133 [Flammable Solids]: Flammable/combustible material. May be ignited by friction, heat, sparks or flames. Some may burn rapidly with flare-burning effect. Powders, dusts, shavings, borings, turnings or cuttings may explode or burn with explosive violence. Substance may be transported in a molten form at a temperature that may be above its flash point. May re-ignite after fire is extinguished. (ERG, 2016)|Flammable - 2nd degree

|Warning|H228 (99.02%): Flammable solid [Danger Flammable solids]|P210, P240, P241, P280, and P370+P378|Aggregated GHS information provided by 1831 companies from 11 notifications to the ECHA C&L Inventory.|H228: Flammable solid [Danger Flammable solids]|P210, P240, P241, P260, P264, P270, P280, P309+P311, P370+P378, P405, and P501

Excerpt from ERG Guide 133 [Flammable Solids]: SMALL FIRE: Dry chemical, CO2, sand, earth, water spray or regular foam. LARGE FIRE: Water spray, fog or regular foam. Move containers from fire area if you can do it without risk. Fire Involving Metal Pigments or Pastes (e.g. "Aluminum Paste") Aluminum Paste fires should be treated as a combustible metal fire. Use DRY sand, graphite powder, dry sodium chloride-based extinguishers, G-1® or Met-L-X® powder. Also, see ERG Guide 170. FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Cool containers with flooding quantities of water until well after fire is out. For massive fire, use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. (ERG, 2016)

Excerpt from ERG Guide 133 [Flammable Solids]: As an immediate precautionary measure, isolate spill or leak area for at least 25 meters (75 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 100 meters (330 feet). FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 133 [Flammable Solids]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch or walk through spilled material. SMALL DRY SPILL: With clean shovel, place material into clean, dry container and cover loosely; move containers from spill area. LARGE SPILL: Wet down with water and dike for later disposal. Prevent entry into waterways, sewers, basements or confined areas. (ERG, 2016)

Excerpt from ERG Guide 133 [Flammable Solids]: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. (ERG, 2016)

/GUIDE 133 FLAMMABLE SOLIDS/ Fire or Explosion: Flammable/combustible material. May be ignited by friction, heat, sparks or flames. Some may burn rapidly with flare burning effect. Powders, dusts, shavings, borings, turnings or cuttings may explode or burn with explosive violence. Substance may be transported in a molten form at a temperature that may be above its flash point. May re-ignite after fire is extinguished.|/GUIDE 133 FLAMMABLE SOLIDS/ Health: Fire may produce irritating and/or toxic gases. Contact may cause burns to skin and eyes. Contact with molten substance may cause severe burns to skin and eyes. Runoff from fire control may cause pollution.|/GUIDE 133 FLAMMABLE SOLIDS/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area for at least 25 meters (75 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas.|/GUIDE 133 FLAMMABLE SOLIDS/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection.|For more DOT Emergency Guidelines (Complete) data for BORNEOL (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials. Borneol is included on the dangerous goods list.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article. Borneol is included on the dangerous goods list.

| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.| 2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.| 0 - Materials that in themselves are normally stable, even under fire conditions.

Borneol has been detected in the final effluent from one plant in each of the following industries: paint and ink, inorganic chemicals, textile mills, rubber processing, electronics, and mechanical products, and in the final effluent from two plants in the pulp and paper industry(1). Borneol was identified in one sample taken downstream of a publicly owned treatment works in Sauget Il. in June 1980(2). Borneol was identified in 1 out of 2 secondary effluent samples from Fort Polk, LA, in November 1980, at a concentration of 0.054 ug/L(3). Borneol was detected in raw sewage samples collected in May 2007 from a municipal treatment plant in China(4).

SOIL: In a study reported in 1983, borneol was identified in the soil extract from a site at a pine-tar manufacturer in Gainesville, FL which closed in 1967(1).

SOURCE DOMINATED: Borneol was detected in the emissions of 2 (Sabalpine Fir and Big Sagebrush) out of 14 vegetation species in forests near Hayden CO; emission rates for both species were reported as 0.1 ug C/hr/gram dry weight(1).

Borneol has been identified in tobacco smoke and tobacco substitute smoke and in tobacco collected from cigarettes(1). Borneol has been identified as a constituent in the volatile emissions from 2 out of 10 household products, detergents and liquid floor wax(2) and was identified in the volatile emissions from domestic garden waste(3).

Toxicity

IDENTIFICATION AND USE: Borneol is a solid. It is used as a flavoring, and as a medication, including traditional Chinese medicine. HUMAN EXPOSURE AND TOXICITY: Borneol does not present a concern for skin sensitization. Toxicity is essentially indistinguishable from that of camphor. Human peripheral blood lymphocytes were exposed to varying concentrations of l-borneol in DMSO up to 600 ug/mL for 4 hr, with and without metabolic activation and 24 hr without metabolic activation. Under the conditions of the study, l-borneol was considered non-clastogenic. ANIMAL STUDIES: As with camphor, laboratory animals appear to be much less susceptible to borneol toxicity than man. Borneol increased the activity of CYP2D in rats orally treated by borneol for 7 days. Borneol has been evaluated for antinociceptive and anti-inflammatory activities in mice. Borneol produced a significant reduction of the nociceptive behavior at the early and late phases of paw licking and reduced the writhing reflex in mice. When the hot plate test was conducted, borneol (in higher dose) produced an inhibition of the nociceptive behavior. Additionally, borneol-treated mice had reduced the carrageenan-induced leukocytes migration to the peritoneal cavity. The mutagenic potential of borneol was assessed in an Ames test with Salmonella typhimurium strains TA1535, TA1537, TA1538, TA98 and TA100 treated with borneol at concentrations up to 5000 ug/ plate in the presence and absence of metabolic activation. Other studies confirming a lack of mutagenic potential in S. typhimurium strains TA98 and TA100 have been published. Under the conditions of the study, borneol is considered not mutagenic in bacteria.

To investigate the enhancing effect of borneol on transcorneal permeation of compounds with different hydrophilicities and molecular sizes. Six compounds, namely rhodamine B, sodium-fluorescein, fluorescein isothiocyanate (FITC) dextrans of 4, 10, 20 and 40 kDa were selected as model drugs. Permeation studies were performed using excised cornea of rabbits by a Franz-type diffusion apparatus. The safety of borneol was assessed on the basis of corneal hydration level and Draize eye test. The application of 0.2% borneol to the cornea increased the apparent permeability coefficient by 1.82-(p<0.05), 2.49-(p<0.05), 4.18-(p<0.05), and 1.11-fold (not significant) for rhodamine B, sodium-fluorescein, FITC-dextrans of 4 and 10 kDa, respectively. No significant permeability enhancement of FITC dextrans of 10, 20 and 40 kDa with borneol was found compared to control. The permeability coefficient enhanced by 0.2% borneol was linear correlated to the molecular weight of model drugs (R(2)=0.9976). With the 0.05%, 0.1% and 0.2% borneol application, the corneal hydration values were <83% and Draize scores were <4. Borneol may improve the transcorneal penetration of both hydrophilic and lipophilic compounds without causing toxic reactions, especially hydrophilic ones. Furthermore, 0.2% borneol can enhance the permeation of hydrophilic compounds with molecular weight

LD50 Mice oral 1059 mg/kg

Borneol occurs in citrus peel oils (orange, lemon, lime), cinnamon leaf, cassia leaf, ginger, coriander seed, laurel, Ocimumbasillum, Thymus vulgaris, and Curcuma aeruginosa Roxb(1). Borneol is a component in various plants, plant tissues, and many plant essential oils(2,3).|Both D- and L- isomeric forms of borneol are naturally occurring(1). The most frequently encountered is L-borneol, characteristic of Compositae, Graminaceae and almost all Pinaceae, as well as in Blumea balsamifera. D-Borneal is characteristic of Cupressaceae, Zingiberaceae, lavenderm lavadin and spike oils, as well as oil from Dryobalanops aromatica Gaertn., Dipterocarpaceae(1,2).

Borneol's production and use as a food flavoring, in fragrances, and in the manufacture of its esters(1) may result in its release to the environment through various waste streams(SRC). Borneol has been identified in tobacco smoke and tobacco substitute smoke and in tobacco collected from cigarettes(2).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 76(SRC), determined from a structure estimation method(2), indicates that borneol is expected to have high mobility in soil(SRC). Volatilization of borneol from moist soil surfaces may be expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.38X10-5 atm-cu m/mole(3) based upon its vapor pressure, 5.02X10-2 mm Hg(4), and water solubility, 738 mg/L(5). Borneol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 5.02X10-2 mm Hg at 25 °C(4). Utilizing the Japanese MITI test, 97% of the Theoretical BOD was reached in 4 weeks indicating that biodegradation is an important environmental fate process in soil(6).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 76(SRC), determined from a structure estimation method(2), indicates that borneol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces may be expected(3) based upon an estimated Henry's Law constant of 1.38X10-5 atm-cu m/mole(4) derived from its vapor pressure, 5.02X10-2 mm Hg(5), and water solubility, 738 mg/L(6). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2.2 days and 29 days, respectively(SRC). According to a classification scheme(7), an estimated BCF of 30(SRC), from its log Kow of 2.69(8) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Utilizing the Japanese MITI test, 97% of the Theoretical BOD was reached in 4 weeks indicating that biodegradation is an important environmental fate process in water(9).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), borneol, which has a vapor pressure of 5.02X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase borneol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 1.4 days(SRC), calculated from its rate constant of 1.14X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Borneol does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of borneol with photochemically-produced hydroxyl radicals has been estimated as 1.14X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1.4 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Borneol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Borneol does not contain chromophores that absorb at wavelengths >290 nm(3) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 30 was calculated in fish for borneol(SRC), using a log Kow of 2.69(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of borneol can be estimated to be 76(SRC). According to a classification scheme(2), this estimated Koc value suggests that borneol is expected to have high mobility in soil.

The Henry's Law constant for borneol is estimated as 1.38X10-5 atm-cu m/mole(SRC) derived from its vapor pressure, 5.0210-2 mm Hg(1), and water solubility, 738 mg/L(2). This Henry's Law constant indicates that borneol is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 2.2 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 29 days(SRC). Borneol's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Borneol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 5.02X10-2 mm Hg(1).

GROUNDWATER: Borneol was detected in groundwater samples from wells at an abandoned creosote manufacturing facility in Conroe, TX taken in June 1983 and January 1985(1). Sampling conducted in August 1983 indicated borneol concentrations ranging from 1.5 to 203.6 ng/mL(2).|DRINKING WATER: Borneol was identified in New Orleans LA drinking waters as of November 1974(1). In a report dated 1975, borneol was listed as a compound identified in U.S. drinking waters(2).

Borneol has been identified as a constituent in the volatile extract from fresh rhizomes of ginger and ginger essential oil (Zingiber officinale Roscoe)(1,2). Borneol has been identified as a flavor constituent of Pine Sprout Tea from Korean red pine trees (Pinus densiflora Seib. Et Zucc.)(3).

Occupational exposure to borneol may occur through inhalation and dermal contact with this compound at workplaces where it is produced or used. Limited monitoring data indicate that the general population may be exposed to borneol via inhalation of ambient air, ingestion of food and drinking, and dermal contact with consumer products containing borneol. (SRC)

Drug Information

Helps relieve the local itching and discomfort associated with hemorrhoids. Temporarily shrinks hemorrhoidal tissue and relieves burning. Temporarily provides a coating for relief of anorectal discomforts. Temporarily protects the inflamed, irritated anorectal surface to help make bowel movements less painful.|For the temporary relief of minor aches and pains of muscles and joints due to: arthritis - strains - bruises - sprains - simple backaches|Antibacterial|Borneol is consumed excessively in China and Southeast Asian countries particularly in combined formula for preventing cardiovascular disease, but few studies were conducted on its effects on thrombosis. In this study, the antithrombotic and antiplatelet activities of borneol were investigated on thrombosis in vivo and on platelet aggregation ex-vivo. In addition, the coagulation parameters and influence on fibrinolytic activity were also assessed. The results showed that borneol had concentration dependent inhibitory effects on arterio-venous shunt and venous thrombosis but no effect on ADP and AA-induced platelet aggregation. Meanwhile, borneol prolonged the coagulation parameters for prothrombin time (PT) and thrombin time (TT), but did not show any fibrinolytic activity. It suggested that the antithrombotic activity of borneol and its action in combined formula for preventing cardiovascular diseases might be due to anticoagulant activity rather than antiplatelet activity. /Traditional medicine/|For more Therapeutic Uses (Complete) data for BORNEOL (6 total), please visit the HSDB record page.

4. 4= Very toxic: probable oral lethal dose (human) 50-500 mg/kg, between one teaspoon and one oz for 70 kg person (150 lb).

To develop a GC-FID method to determine borneol's concentration in mouse tissues, and to investigate the tissue distribution after intravenous and intranasal administrations of borneol, mouse brains, hearts, livers, spleens, lungs and kidneys were collected at 1, 3, 5, 10, 20, 30, 60, 90, 120 min after administration of borneol with the dose of 30.0 mg/kg. The drug in tissues was extracted with ethyl acetate, and borneol's concentration detected by GC, with octadecane as the internal standard. The calibration curve showed a good linear relationship. Extraction recoveries, inter-day and intra-day precisions and stability were in conformity with the analytical requirements of biological samples. Borneol was mainly distributed in most tissues, more in heart, brain and kidney, and less in liver, spleen and lung. The established GC-FID method is applicable for content determination of borneol in tissues. After intravenous and intranasal administrations in mice, borneol is mainly distributed in abundant blood-supply tissues. After intranasal administration, brain tissues showed the highest target coefficient and target effectiveness.|... In order to understand the blood and brain pharmacokinetics after intravenous, intranasal, or oral administration and to investigate the superiority and feasibility of intranasal administration, a simple gas chromatographic (GC) method with flame ionization detection (FID) was developed for the quantification of borneol. Blood samples and brain were collected from mice at 1, 3, 5, 10, 20, 30, 60, 90, and 120 min after intravenous, intranasal, or oral administration of borneol at a dosage of 30.0 mg/kg. Sample preparations were carried out by liquid-liquid extraction with an internal standard solution of octadecane. The pharmacokinetic parameters were calculated /using computer software/. The calibration curves were linear in the range of 0.11-84.24 ug/mL and 0.16-63.18 ug/g for borneol in plasma and brain, respectively. The methodological and extraction recoveries were both in the range of 85%-115%. The intra-day and inter-day variabilities for plasma and brain samples were

Excerpt from ERG Guide 133 [Flammable Solids]: Fire may produce irritating and/or toxic gases. Contact may cause burns to skin and eyes. Contact with molten substance may cause severe burns to skin and eyes. Runoff from fire control may cause pollution. (ERG, 2016)

Excerpt from ERG Guide 133 [Flammable Solids]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. Removal of solidified molten material from skin requires medical assistance. Keep victim calm and warm. (ERG, 2016)

Immediate First Aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Camphor and related compounds/|Basic Treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Anticipate seizures and minimize all external stimuli. Treat seizures as necessary ... . Monitor for shock and treat as necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Camphor and related compounds/|Advanced Treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or is in respiratory distress. Monitor and treat cardiac arrhythmias as necessary ... . Start IV administration of D5W TKO. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Camphor and related compounds/

/HUMAN EXPOSURE STUDIES/ Based on the available data for the read across material (l-borneol, CAS # 464-45-9) and application of the non-reactive DST, borneol does not present a concern for skin sensitization. The chemical structure of these materials indicates that they would not be expected to react directly with skin proteins. In the human maximization test, two reactions were observed in a panel of 25 subjects to l-borneol; however these were considered questionable due to the presence of concurrent test materials for which numerous strong reactions were observed. The human maximization test was repeated, utilizing the same concentration; no reactions (0/25) indicative of sensitization were observed to l-borneol. In another human maximization test, no reactions indicative of sensitization were observed with 8% l-borneol in petrolatum. /l-Borneol/|/GENOTOXICITY/ There are no data assessing the clastogenicity of borneol. Read across material l-borneol (CAS # 464-45-9), was assessed for clastogenic potential in a GLP compliant in vitro micronucleus study conducted in accordance with OECD TG 487. Human peripheral blood lymphocytes were exposed to varying concentrations of l-borneol in DMSO up to 600 ug/mL for 4 hr, with and without metabolic activation and 24 hr without metabolic activation. Under the conditions of the study, l-borneol was considered non-clastogenic./l-Borneol/|/ALTERNATIVE and IN VITRO TESTS/ The beta-amyloid (Abeta) peptide aggregation with accompanying oxidative stress plays the major role in the pathogenesis of Alzheimer's disease (AD). Some natural compounds, including borneol, shed promising light on AD treatment. The present study was designed to investigate the antioxidative, antiapoptotic effects, and neuroprotection of borneol in human neuroblastoma cells (SH-SY5Y). Oxidative stress was induced by administering 50 uM Abeta into SH-SY5Y cells. Neuroprotective effect of commercially available borneol was examined by determining cell viability with the MTT assay. Intracellular reactive oxygen species (ROS) generation was measured using a fluorometer with further examination of heme oxygenase-1 (HO-1) and nuclear factor-erythroid 2 p45-related factor 2 (Nrf2) expression. Apoptosis was examined by measuring the ratio of B-cell lymphoma 2 (Bcl-2)/Bcl-2-associated X protein (Bax). Our data indicated that Abeta-induced cell cytotoxicity was inhibited by 100 uM of (-) and (+) borneol treatment. Treatment of borneol significantly decreased ROS generation (p<0.01). The expression of HO-1 and nuclear translocation of Nrf2 were increased by Abeta treatment. This nuclear translocation of Nrf2 was further increased by administration of borneol. Compared with the Abeta treated group, the (+) borneol treated group significantly increased Bcl-2 expression with decreased expression of Bax. Borneol protected SH-SY5Y cells against Abeta-induced toxicity, exerted an antioxidative effect and suppressed apoptosis. It increases our knowledge about neuroprotective mechanism of borneol, and it is hopeful to be a candidate compound for developing therapeutic drug for the prevention and treatment of AD and other Abeta-related neurodegenerative diseases.|/ALTERNATIVE and IN VITRO TESTS/ Curcumin (Cur), an active ingredient from the rhizome of the plant Curcuma longa, has wide anticancer activities. However, due to its poor solubility and hence poor absorption, Cur has limited clinical applications. It is therefore important to develop an effective method to improve its absorption. Natural borneol (NB), a terpene and bicyclic organic compound, has been extensively used as a food additive, and our previous studies show that it can improve the uptake of Cur in cancer cells. However, the anticancer mechanism of NB/Cur remains unclear. In this study, the effects of NB/Cur on HepG2 cells were investigated by proteomic analysis. The results showed that 32 differentially expressed proteins identified by matrix assisted laser desorption ionization time-of-flight mass spectrometry were significantly changed after NB/Cur treated HepG2 cells for 24 h. Moreover, 17 proteins increased and 12 proteins decreased significantly. Biological progress categorization demonstrated that the identified proteins were mainly associated with cell cycle and apoptosis (28.1%). Subcellular location categorization exhibited that the identified proteins were mainly located in nucleus (28.1%) and mitochondrion (21.9%). Among of all proteins, we selected three differential proteins (hnRNPC1/C2, NPM, and PSMA5), which were associated with the p53 pathway. Down-regulation of hnRNPC1/C2 and NPM contributed to the enhancement of phosphorylated p53. Activated p53 and down-regulation of PSMA5 resulted in an increase in p21 protein. Further studies showed that NB/Cur induced reactive oxygen species (ROS) generation, indicating that ROS might be upstream of the G2/M arrest signaling pathway. In summary, the results exhibited the whole proteomic response of HepG2 cells to NB/Cur, which might lead to a better understanding of its underlying anticancer mechanisms.|/OTHER TOXICITY INFORMATION/ / Toxicity is essentially indistinguishable from that of camphor.

borneol

endo-Borneol Use and Manufacturing

Methods of Manufacturing

It is made by dissolving camphor in ethanol with metallic sodium or by reducing it with new ecological hydrogen. It is made from pinene treated with hydrochloric acid and magnesium powder.

Uses

Used in the manufacture of borneol esters, spices, etc.


Fragrance Ingredients

PAIN FREE - menthol, methyl salycilate, borneol ointment; Menthol 2%, Methyl Salicylate 1%, Borneol 2%|Grades: technical.|Commercial borneol is often levorotatory ... and contains (-)-borneol and up to 40% isoborneol.|MA YING LONG HEMORRHOIDAL- moschus artifactus, bovis calculus artifactus, margarita, borneolum syntheticum, succinum, calamina (calcined), borax ointment; Moschus - Bovis Calculus - Margarita (Hyriopsis Cuming II) Borneolum syntheticum - Calamina (Calcined) Borax - Succinum|For more Formulations/Preparations (Complete) data for BORNEOL (6 total), please visit the HSDB record page.

Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, (1S,2R,4S)-: ACTIVE|All other chemical product and preparation manufacturing|Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, (1R,2S,4R)-rel-: ACTIVE|The major product in perfumery, by far, is isobornyl acetate; borneol being used at about one-tenth the volume of the former. The most important use for isoborneol is as an intermediate for camphor.

Constituents of lavandula dentata oil (including borneol) were identified by two GLS-MS systems.|Borneol was identified in sage oil by TLC.|In this work, microwave-assisted extraction (MAE) followed by gas chromatography with flame ionization detector (GC-FID) was developed for the rapid determination of camphor and borneol in three traditional Chinese medicines (TCM): Chrysanthemi indici, Flos Chrysanthemi indici and Amomum villosum lour. The optimal MAE conditions obtained were: acetone for solvent, with solvent having sample ratio of 12:1 (v/w); microwave power of 380 W, and an irradiation time of 4 min. Method validations were also studied. To demonstrate the proposed method, ultrasonic-assisted extraction (UAE) and steam distillation (SD), followed by GC-FID, were used to analyze camphor and borneol in the three TCMs. The close results were obtained by the three methods. The results showed that the proposed MAE-GC-FID is a simple, rapid, and reliable method for quantitative analysis of camphor and borneol in TCM, and is also a potential tool for TCM quality assessment.

Rat plasma samples were prepared using liquid-liquid microextraction: 70 uL of plasma sample (containing 125 nmol/L naphthalene as the internal standard) was extracted with 35 uL of n-hexane. The resulting n-hexane extract (20 uL) was introduced into a gas chromatography/mass spectrometry system using programmable temperature vaporizing-based large-volume injection. The assay was validated to demonstrate its reliability for the intended use. Using this assay, pharmacokinetic studies of Bingpian, synthetic Bingpian, and Fufang-Danshen tablets (containing synthetic Bingpian) were conducted in rats. ... The extraction efficiency for the analytes and the internal standard from plasma was almost constant with decrease in n-hexane-to-plasma volume ratio, thus enabling a small volume of extracting solvent to be used for sample preparation, and enhancing the assay sensitivity. The lower quantification limit for measuring borneol, isoborneol, and camphor in plasma was 0.98 nmol/L, which was 33-330 times more sensitive than those reported earlier for Bingpian and synthetic Bingpian. The applicability of the miniaturized liquid-liquid extraction technique could be extended to measure other volatile and nonvolatile medicinal compounds in biomatrices, which can be predicted according to the analytes' octanol/water distribution coefficient (logD) and acid dissociation constant (pKa).

Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index|Fire Hazards -> Flammable - 2nd degree|Cosmetics -> Undefined function

Flavoring Agents

Computed Properties

Molecular Weight:154.25
XLogP3:2.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:154.135765193
Monoisotopic Mass:154.135765193
Topological Polar Surface Area:20.2
Heavy Atom Count:11
Complexity:185
Defined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Tolerance to hypoxia

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Registered Holders

  • Hunan Songyuan Biotech Co., Ltd.

    China China
    Inactive

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