98-55-5 Usage
Description
(-)-alpha terpineol is the alpha form of terpineol, a naturally monoterpene alcohol that can be isolated from various kinds of sources such as cajuput oil, pine oil, and petitgrain oil. The alpha form is the major constituent of terpineol. It is a common component in perfumes, cosmetic and flavors. It is also a kind of solvent used for extracting natural spices and as a kind of solvent of acetate fibers. Moreover, it exhibited strong and broad antimicrobial activity against fungi, bacteria and virus. Study has demonstrated that is antibacterial (bactericidal) effect originated from its destroying effect on the cell wall and cell membrane of bacteria. It also has certain anticonvulsant activity.
References
de Sousa, Damiao Pergentino, Lucindo Quintans Jr, and Reinaldo Nóbrega de Almeida. "Evolution of the anticonvulsant activity of α-terpineol."Pharmaceutical Biology 45.1 (2007): 69-70.
Park, Soon-Nang, et al. "Antimicrobial effect of linalool and α- terpineol against periodontopathic and cariogenic bacteria." Anaerobe 18.3 (2012): 369-372.
Dabbah, Roger, V. M. Edwards, and W. A. Moats. "Antimicrobial action of some citrus fruit oils on selected food-borne bacteria." Applied microbiology19.1 (1970): 27-31.
Chemical Properties
Different sources of media describe the Chemical Properties of 98-55-5 differently. You can refer to the following data:
1. Clear colorless liquid after melting
2. α-Terpineol is a colorless,
crystalline solid, smelling of lilac. The most important commercial grade of
terpineol consists of a liquid mixture of isomers that contains mainly α-terpineol
and a considerable amount of ?γ-terpineol. This mixture has a stronger lilac odor
than does pure crystalline α-terpineol.
Hydrogenation of α-terpineol yields p-menthan-8-ol. Terpineol is readily dehydrated
by acids, yielding a mixture of unsaturated cyclic terpene hydrocarbons.
Under mildly acidic conditions, terpin hydrate is formed. The most important reaction for the fragrance industry is esterification, particularly acetylation to terpinyl
acetate.Terpineol with its typical lilac odor is one of the most frequently used fragrance
substances. It is stable and inexpensive and is used in soaps and cosmetics.
3. α-Terpineol has a characteristic lilac odor with a sweet taste reminiscent of peach on dilution.
Occurrence
Reported found in more than 150 derivatives from leaves, herbs and flowers; the d-, l- and dl-isomers are known: the d-form is found in the essential oils from Cupressaceae in general; also in the oils of Elettaria cardamomum, star anise, marjoram, clary sage, neroli and others. The l-form is found in Satureia montana, lavandin, cajeput, lime, lemon, cinnamon leaves and the distillates from Pinaceae (with exception of Pinus silvestris, which contains d-terpineol together with racemic form); likewise, Nectandra elaiophora (wood) and petitgrain bigarade. The racemic form is found in cajenne linalool, Thymus caespititius, cajeput, Eucalyptus globulus; mixed with the l-form it is found in petitgrain; a nondefined form of terpineol has been reported in the bitter orange. Reported found in over 260 natural sources including apple, apple juice, apricot, sweet and sour cherry, citrus peel oils and juices, orange, lemon, lime, grapefruit, tangerine, mandarin peels oils and juices, bergamot, cranberry, blueberry, black currant, raspberry, strawberry, guava, grapes, raisin, melon, papaya, peach, pear, pineapple, carrot, celery, peas, potato, bell pepper, tomato, anise, cinnamon, clove, cumin seed, ginger, Mentha oils, pepper, mace, parsley, nutmeg, thyme, Gruyere cheese, parmesan cheese, butter, cooked chicken and beef, hop oil, beer, cognac, rum, wines, tea, nuts, honey, avocado, passion fruit, prune, plums, beans, mushroom, sweet and wild marjoram, starfruit, mango, tamarind, parsnip root, cardamom, coriander seed, rice, quince, litchi, calamus, dill, licorice, lovage root, juniper berry, corn oil, laurel, sweet and bitter fennel, wort, elderberry, loquat, myrtle berry, rosemary, buchu oil, Bourbon vanilla, mountain papaya, turmeric, clary sage, lemon balm, nectarines, naranjilla fruit, cape gooseberry and sea buckthorn.
Uses
Different sources of media describe the Uses of 98-55-5 differently. You can refer to the following data:
1. A naturally-occuring monoterpene alcohol.Alpha-terpineol is used as an antioxidant, antiseptic, antihypernociception and anti-inflammatory. It is also used as a solvent. It is an important ingredient of pine oil disinfectants. Further, it is used as a fragrance in perfumes, fat denaturant for soap production and synthetic flavoring agent.
2. Shows antioxidant effects. Antiseptic.
is present in many extracted oils of various plant species, acts as an antihypernociception and anti-inflammatory.
Definition
ChEBI: A terpineol that is propan-2-ol substituted by a 4-methylcyclohex-3-en-1-yl group at position 2.
Preparation
Although α-terpineol occurs in many essential oils, only small
quantities are isolated, for example, by fractional distillation of pine oils.
A common industrial method of α-terpineol synthesis consists of the hydration
of α-pinene or turpentine oil with aqueous mineral acids to give crystalline
cis-terpin hydrate (mp 117 °C), followed by partial dehydration to α-terpineol.
Suitable catalysts are weak acids or acid-activated silica gel.
Selective conversion of pinene, 3-carene, and limonene or dipentene to terpineol,
without terpin hydrate formation is also used. Addition of organic acids (weak
acids require catalytic amounts of mineral acids) produces terpinyl esters, which
are subsequently hydrolyzed to terpineol, sometimes in situ.
Aroma threshold values
Detection: 280 to 350 ppb. Aroma characteristics in 1% ethanol: pine-like, woody and resinous with a slight cooling lemon and lime citrus nuance, and a floral dry out.
Taste threshold values
Taste characteristics at 2 to 25 ppm: woody, terpy, lemon and lemon–lime-like with a slight herbal and floral nuance. Taste characteristics at 10 to 25 ppm: citrus woody with a lemon and lime nuance. It has a slight soapy mouthfeel.
General Description
α-Terpineol is a monoterpene alcohol. It is one of the components responsible for the antifungal activity of Melaleuca alternifolia (tea tree) essential oil. The reaction rate constant of α-terpineol with OH radical and ozone was found to be (1.9±0.5)×10-10cm3 molecule-1s-1 and (3.0±0.2)×10-16cm3 molecule-1s-1, respectively.
Flammability and Explosibility
Nonflammable
Synthesis
Obtained from terpin hydrate by splitting off water; from pentane tricarboxylic acid by cyclization, followed by esterification to the hydroxy ester, then the unsaturated ester and Grignard to terpineol; also from isoprene and methyl vinyl ketone, using methyl magnesium iodide.
Check Digit Verification of cas no
The CAS Registry Mumber 98-55-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 8 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 98-55:
(4*9)+(3*8)+(2*5)+(1*5)=75
75 % 10 = 5
So 98-55-5 is a valid CAS Registry Number.
98-55-5Relevant articles and documents
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.
Nickel Hydride Catalyzed Cleavage of Allyl Ethers Induced by Isomerization
Kathe, Prasad M.,Berkefeld, Andreas,Fleischer, Ivana
supporting information, p. 1629 - 1632 (2021/02/09)
This report discloses the deallylation of O - and N -allyl functional groups by using a combination of a Ni-H precatalyst and excess Bronsted acid. Key steps are the isomerization of the O - or N -allyl group through Ni-catalyzed double-bond migration followed by Bronsted acid induced O/N-C bond hydrolysis. A variety of functional groups are tolerated in this protocol, highlighting its synthetic value.
Preparation of α-Terpineol from Biomass Resource Catalysed by Acid Treated Montmorillonite K10
Sekerová, Lada,?erná, Hana,Vysko?ilová, Eli?ka,Vrbková, Eva,?erveny, Libor
, p. 2673 - 2683 (2021/01/15)
Abstract: A new type of heterogeneous catalyst for hydration of α-pinene was prepared. Montmorillonite K10 was treated by various acids (H2SO4, HCl, HNO3, and ClCH2COOH) and successfully used for the mentioned reaction. The used characterization techniques showed that the acid treatment improved the properties of K10 important for the catalytic activity (SBET and acidity). On the other hand, the morphology and particle size distribution remained the same. Regarding the selectivity (side and consecutive reactions can proceed), the optimal reaction conditions were found (temperature, type of the catalyst, amount of the catalyst, molar ratio α-pinene:?water, type of water, solvent). Using the optimal reaction conditions, 60% conversion of α-pinene was achieved with 45% selectivity to α-terpineol (80?°C, 25 wt% of K10/HCl, or K10/H2SO4, nα-pinene:nwater 1:7.5, 1,4-dioxane as a solvent, 24?h). Higher conversions of α-pinene, as well as higher selectivity to α-terpineol, were achieved using all acid treated K10 in comparison to raw K10. Considering the heterogeneous form of prepared catalysts, its availability, low price and easy method of preparation, these catalysts dispose of a large potential for application as catalysts for hydration reactions. Graphic Abstract: [Figure not available: see fulltext.].
