464-45-9 Usage
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 .
Chemical Properties
white to light yellow crystalline powder or
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.
History
Borneol has been widely used worldwide. It has been systematically studied since 1803 in Dutch literature. This might be because borneol was originated from Indonesia which had been the colony of the Netherlands since the seventeenth century. Stockman reviewed the borneol systematically and conducted the preliminary pharmacological experiments. The current pharmacological studies of borneol focus on crossing blood-brain barrier and its mechanism, as well as promoting the penetration of blood-brain barrier after compatibility with other drugs, which has been started by Qizhong Mo in Shanghai Institute of Materia Medica, Chinese Academy of Sciences since 1982 . Qide Wu et al. synthesized a series of ester derivatives of natural borneol and studied its biological properties. It was found that (+) – 4-methoxybenzoic acid borneol ester had a significant effect on the opening of the blood-brain barrier and was less toxic than borneol . Because of the unique chemical structure of borneol and relatively low molecular weight, borneol is often modified to observe whether the drug has such pharmacological effects of antitumor, increasing the penetration of blood-brain barrier, antibacterial, antioxidant, and others. Up to date, there is no druggability report based on borneol modification.
Uses
Different sources of media describe the Uses of 464-45-9 differently. You can refer to the following data:
1. (-)-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.
2. (-)-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
General Description
(-)-Borneol is an enantiomer. It is a bicyclic monoterpene compound used gengrally for analgesia and anaesthesia. It is considered as positive modulators of GABA receptors.
Flammability and Explosibility
Flammable
Pharmacology
The main pharmacological effects of borneol include anti-inflammatory, antibacterial, central nervous system, and antifertility effects . Guangchi Jiang found that intraperitoneal injection of borneol at 3.5 mL/kg can significantly inhibit foot swelling caused by egg white in rats. Borneol can inhibit and kill Staphylococcus aureus, B-type Streptococcus, and other five common cells with the minimum inhibitory concentration (MIC) of 1.0–2.0% and the lowest bactericidal concentration (MFC) of 1.5–2.0%. There was significant odinopoeia effect on the late pregnant mice after given 112 mg/kg borneol. Qide Liu et al. found that 10% borneol paraffin oil at the dose of 1 mg/kg by oral gavage can significantly increase the concentration of gentamicin in rat brain tissue, suggesting that borneol can change the blood-brain barrier permeability. The current mechanisms of anti-inflammatory effects include inhibition of inflammatory factors of interleukin-1β, tumor necrosis factor-α, and cell adhesion molecule-1 expression. The mechanisms of central nervous system effects are involved in inhibiting p-glycoprotein, opening the intercellular tight junction, increasing the number of pinocytotic vesicles, and improving the phospholipid molecule arrangement of epithelial cell membrane. In addition, borneol also affects the level of nitric oxide and inhibits the elevation of Ca2+ concentration.
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.
Safety Profile
Mddly toxic by
ingestion. A skin irritant. When heated to
decomposition it emits acrid smoke and
irritating fumes. See also ALCOHOLS.
Check Digit Verification of cas no
The CAS Registry Mumber 464-45-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,6 and 4 respectively; the second part has 2 digits, 4 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 464-45:
(5*4)+(4*6)+(3*4)+(2*4)+(1*5)=69
69 % 10 = 9
So 464-45-9 is a valid CAS Registry Number.
InChI:InChI=1/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
464-45-9Relevant articles and documents
Enantioselective Construction of Modular and Asymmetric Baskets
Badji?, Jovica D.,Finnegan, Tyler J.,Gunther, Michael J.,Pavlovi?, Radoslav Z.,Wang, Xiuze
supporting information, p. 25075 - 25081 (2021/10/25)
The precise positioning of functional groups about the inner space of abiotic hosts is a challenging task and of interest for developing more effective receptors and catalysts akin to those found in nature. To address it, we herein report a synthetic methodology for preparing basket-like cavitands comprised of three different aromatics as side arms with orthogonal esters at the rim for further functionalization. First, enantioenriched A (borochloronorbornene), B (iodobromonorbornene), and C (boronorbornene) building blocks were obtained by stereoselective syntheses. Second, consecutive A-to-B and then AB-to-C Suzuki–Miyaura (SM) couplings were optimized to give enantioenriched ABC cavitand as the principal product. The robust synthetic protocol allowed us to prepare (a) an enantioenriched basket with three benzene sides and each holding either tBu, Et, or Me esters, (b) both enantiomers of a so-called “spiral staircase” basket with benzene, naphthalene, and anthracene groups surrounding the inner space, and (c) a photo-responsive basket bearing one anthracene and two benzene arms.
Molecular cloning and functional characterization of a two highly stereoselective borneol dehydrogenases from Salvia officinalis L
Drienovská, Ivana,Kolanovi?, Dajana,Chánique, Andrea,Sieber, Volker,Hofer, Michael,Kourist, Robert
, (2020/01/11)
Enzymes for selective terpene functionalization are of particular importance for industrial applications. Pure enantiomers of borneol and isoborneol are fragrant constituents of several essential oils and find frequent application in cosmetics and therapy. Racemic borneol can be easily obtained from racemic camphor, which in turn is readily available from industrial side-streams. Enantioselective biocatalysts for the selective conversion of borneol and isoborneol stereoisomers would be therefore highly desirable for their catalytic separation under mild reaction conditions. Although several borneol dehydrogenases from plants and bacteria have been reported, none show sufficient stereoselectivity. Despite Croteau et al. describing sage leaves to specifically oxidize one borneol enantiomer in the late 70s, no specific enzymes have been characterized. We expected that one or several alcohol dehydrogenases encoded in the recently elucidated genome of Salvia officinalis L. would, therefore, be stereoselective. This study thus reports the recombinant expression in E. coli and characterization of two enantiospecific enzymes from the Salvia officinalis L. genome, SoBDH1 and SoBDH2, and their comparison to other known ADHs. Both enzymes produce preferentially (+)-camphor from racemic borneol, but (?)-camphor from racemic isoborneol.
Synthesis method of levo-borneol
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Paragraph 0036; 0039-0041; 0044-0046; 0049-0051; 0054-0055, (2020/09/02)
The invention relates to a synthetic method of L-borneol. The method comprises: reducing di-n-butyltin dichloride to obtain di-n-butyltin dihydride via lithium aluminium hydride, performing a reactionamong 2-camphanone, palladium bis(triphenylphosphine) dichloride and methanol, adding di-n-butyltin dihydride drop by drop while performing uniform stirring, performing a reaction at the room temperature for 1 h, after the reaction is over, performing pressure-reduction rotary evaporation to remove methanol, and performing separation to obtain L-borneol, which is the target compound.
