470-82-6 Usage
Description
Eucalyptol is a bicyclic monoterpene that has been found in Eucalyptus and other plants, including C. sativa and has diverse biological activities, including anti-inflammatory, decongestant, antinociceptive, and insect repellent properties. Eucalyptol (10 μM) inhibits TNF-α, IL-1β, IL-4, and IL-5 production by primary human lymphocytes stimulated by ionomycin and phorbol 12-myristate 13-acetate (PMA; ). It also decreases LPS-induced mucus production by primary human nasal turbinate slices when used at a concentration of 10 μM. Eucalyptol (400 mg/kg) decreases carrageenan-induced hind paw edema in rats and reduces the time spent licking the hind paw in a formalin-induced nociception test in mice. It inhibits A. aegypti mosquitoes from feeding on anesthetized gerbils when applied topically at a concentration of 10% and from laying eggs in an ovipositional bioassay when used at a concentration of 1% in standing water. Formulations containing eucalyptol have been used in mouthwash and cough suppressants.
Chemical Properties
Different sources of media describe the Chemical Properties of 470-82-6 differently. You can refer to the following data:
1. 1,8-Cineole occurs
in many terpene-containing essential oils, sometimes as the main component. For
example, eucalyptus oils contain up to 85% 1,8-cineole and laurel leaf oil contains
up to 70%. It is a colorless liquid with a characteristic odor, slightly reminiscent of
camphor.
1,8-Cineole is one of the few fragrance materials that is obtained exclusively
by isolation from essential oils, especially eucalyptus oils. Technical-grade 1,8-
cineole with a purity of 99.6–99.8% is produced in large quantities by fractional
distillation of Eucalyptus globulus oil. A product essentially free from other products
can be obtained by crystallization of cineole-rich eucalyptus oil fractions
2. Eucalyptol has a characteristic camphoraceous odor and fresh, pungent, cooling taste.
Occurrence
Its name is derived from its presence in the essential oils of Eucalyptus globulus and Melaleuca leucadendron
L. (essential oil of cajeput). It was originally identified in the essential oil of Artemisia maritime and subsequently in a large number
(approx. 270) of other essential oils: rosemary, laurel leaves, clary sage, myrrh, cardamom, star anise, camphor, lavender, peppermint,
Litsea guatemalensis, Luvunga scadens Roxb., Achillea micrantha and Salvia triloba. The essential oil of Eucalyptus polibrac tea
has been reported to contain up to 91% eucalyptol. Also reported found in citrus oils and juices, guava, papaya, cinnamon bark, root
and leaf, ginger, corn mint oil, spearmint, nutmeg, pepper, Thymus zygis, cardamom, cranberry, laurel, pepper, sweet marjoram,
coriander, Spanish origanum, Ocimum basilicum, curcuma, sage, laurel, sweet and bitter fennel, myrtle leaf and berry, pimento and
calamus.
Uses
Different sources of media describe the Uses of 470-82-6 differently. You can refer to the following data:
1. Labelled 1,8-Cineol, the chief constituent of oil of eucalyptus. Used as pharmaceutic aid (flavor).
2. 1,8-Cineol is the chief constituent of oil of eucalyptus. Used as pharmaceutic aid (flavor).
3. eucalyptol is considered an antiseptic. This is a monoterpene compound that provides the fragrance associated with the essential oil of eucalyptus. eucalyptol is also used to fragrance cosmetic preparations.
Preparation
By fractional distillation (170 to 180°C) from those essential oils containing high levels of eucalyptol, such as Eucalyptus
globulus (approx. 60%), and subsequent separation of the product by congealing the distillate.
Aroma threshold values
Detection: 1 to 64 ppb. Aroma characteristics at 1.0%: sweet, cooling, fresh, chemical pine, slightly minty
with a spicy cardamom nuance.
Taste threshold values
Taste characteristics at 5 ppm: cooling, fresh, oily, green, spicy, pine-like.
General Description
Colorless liquid with a camphor-like odor. Spicy cooling taste.
Air & Water Reactions
Highly flammable. Insoluble in water.
Reactivity Profile
Cineole will react with acids and bases.
Fire Hazard
Flash point data for Cineole are not available but Cineole is probably combustible.
Flammability and Explosibility
Flammable
Biochem/physiol Actions
Taste at 30 ppm
Anticancer Research
A statistically significant reduction of cell proliferation was observed compared tothe control cells when tested on RKO cells and human colon cancer cell linesHCT116 injected into the SCID mice. The 1,8-cineole induced apoptosis by inactivatingsurviving and Akt, activating p38, inducing PARP, and cleaving caspase-3(Rodd et al. 2015).
Toxicology
Eucalyptol, a colourless organic compound, is a monoterpenoid and an ether. Among its various uses, eucalyptol is predominantly used as an insecticide and in fragrances (Klocke et al. 1987). The ques- tion of whether eucalyptol could potentiate toxicity has been assessed because of its widespread use in households. When Kunming mice received feed with a high dose of eucalyptol, liver and kidney tissue demonstrated vacuolar and granular degeneration (Xu et al. 2014). When the animals were fed with a subacute dose of eucalyptol, no discernible difference in body weight was observed (Xu et al. 2014). Eucalyptol’s safety profile has been assessed. Fatality after ingestion of eucalyptol oil has been reported; the approximate lethal dose of eucalyptol in the human is between 0.05 and 0.5 mL/kg of body weight (Hindle 1994). When male rats received eucalyptol, eosinophilic protein droplets accumulated in a dose- dependent fashion (Kristiansen and Madsen 1995). However, in a study of mutagenicity using CHO cells, eucalyptol did not induce mutagenicity as evidenced in the sister chromatid exchange assay (Galloway et al. 1987). Likewise, eucalyptol did not induce carcinogenicity in pathogen-free CFLP mice (Roe et al. 1979).
Metabolism
Eucalyptol undergoes oxidation in vivo with the formation of hydroxy cineole, which is excreted as hydroxycineoleglucuronic acid (Williams, 1959).
Purification Methods
Purify 1,8-cineol by dilution with an equal volume of pet ether, then saturate with dry HBr. The precipitate is filtered off, washed with small volumes of pet ether, then cineole is regenerated by stirring the crystals with H2O. It can also be purified via its o-cresol or resorcinol addition compounds. Store it over Na until required. Purify it also by fractional distillation. It is insoluble in H2O but soluble in organic solvents. [IR: Kome et al. Nippon Kagaku Zasshi [J Chem Soc Japan (Pure Chem Sect)] 80 66 1959, Chem Abstr 603 1961, Beilstein 17 II 32, 17/1 V 273.]
Check Digit Verification of cas no
The CAS Registry Mumber 470-82-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,7 and 0 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 470-82:
(5*4)+(4*7)+(3*0)+(2*8)+(1*2)=66
66 % 10 = 6
So 470-82-6 is a valid CAS Registry Number.
470-82-6Relevant articles and documents
A simple, convenient and expeditious approach to cineol
Bugar?i?, Zorica M.,Dunki?, Jelena D.,Mojsilovi?, Biljana M.
, p. 468 - 470 (2004)
A convenient two-step protocol preparation of cineol (1-isopropyl-4-methyl- 7-oxabicyclo-[2,2,1]heptane) from α-terpineol (p-menth-1-en-8-ol) is reported. The phenylselenoetherification of α-terpineol with PhSeX (X = Cl, Br, I) as a key step is described. α-Terpineol reacts with PhSeX to form the corresponding phenylselenoether in short reaction time and in quantitative yield. A subsequent reduction with Bu3SnH to cineol proceeds in high yield (98%)
Thioderivatives of Resorcin[4]arene and Pyrogallol[4]arene: Are Thiols Tolerated in the Self-Assembly Process?
Nemat, Suren J.,Tiefenbacher, Konrad
supporting information, p. 6861 - 6865 (2021/09/14)
Three novel thiol bearing resorcin[4]arene and pyrogallol[4]arene derivatives were synthesized. Their properties were studied with regards to self-assembly, disulfide chemistry, and Br?nsted acid catalysis. This work demonstrates that (1) one aromatic thiol on the resorcin[4]arene framework is tolerated in the self-assembly process to a hexameric hydrogen bond-based capsule, (2) thio-derivatized resorcin[4]arene analogs can be covalently linked through disulfides, and (3) the increased acidity of aromatic thio-substituent is not sufficient to replace HCl as cocatalyst for capsule catalyzed terpene cyclizations.
Requirements for Terpene Cyclizations inside the Supramolecular Resorcinarene Capsule: Bound Water and Its Protonation Determine the Catalytic Activity
Merget, Severin,Catti, Lorenzo,Piccini, Giovannimaria,Tiefenbacher, Konrad
supporting information, p. 4400 - 4410 (2020/03/04)
The elucidation of the requirements for efficient catalysis within supramolecular host systems is an important prerequisite for developing novel supramolecular catalysts. The resorcinarene hexamer has recently been shown to be the first supramolecular catalyst to promote the tail-to-head terpene cyclization in a biomimetic fashion. We herein present the synthesis of a number of resorcinarene-based macrocycles composed of different ratios of resorcinol and pyrogallol units capable of self-assembly and compare the corresponding assemblies regarding their catalytic activity in the cyclization of monoterpenes. The assemblies were investigated in detail with respect to a number of properties including the encapsulation of substrate and ion pairs, the structural incorporation of water, and the response to externally added acid (HCl). The results obtained strongly indicate that water incorporated into the hydrogen-bond network of the self-assembled structure plays an integral role for catalysis, effectively acting as a proton shuttle to activate the encapsulated substrate. These findings are also supported by molecular dynamics simulations, providing further insight into the protonation pathway and the relative energies of the intermediates involved.
Terpene Cyclizations inside a Supramolecular Catalyst: Leaving-Group-Controlled Product Selectivity and Mechanistic Studies
Zhang, Qi,Catti, Lorenzo,Pleiss, Jürgen,Tiefenbacher, Konrad
supporting information, p. 11482 - 11492 (2017/08/30)
The tail-to-head terpene cyclization is arguably one of the most complex reactions found in nature. The hydrogen-bond-based resorcinarene capsule represents the first man-made enzyme-like catalyst that is capable of catalyzing this reaction. Based on noncovalent interactions between the capsule and the substrate, the product selectivity can be tuned by using different leaving groups. A detailed mechanistic investigation was performed to elucidate the reaction mechanism. For the cyclization of geranyl acetate, it was found that the cleavage of the leaving group is the rate-determining step. Furthermore, the studies revealed that trace amounts of acid are required as cocatalyst. A series of control experiments demonstrate that a synergistic interplay between the supramolecular capsule and the acid traces is required for catalytic activity.
Xi:Irritant;
