98-55-5 Usage
Description
Alpha-Terpineol is the alpha form of terpineol, a naturally occurring monoterpene alcohol that can be isolated from various sources such as cajuput oil, pine oil, and petitgrain oil. It is a common component in perfumes, cosmetics, and flavors, and also serves as a solvent for extracting natural spices and acetate fibers. Additionally, alpha-terpineol exhibits strong and broad antimicrobial activity against fungi, bacteria, and viruses, with its antibacterial effect attributed to its destructive impact on the cell wall and cell membrane of bacteria. It also possesses anticonvulsant activity.
Uses
Used in Perfume Industry:
Alpha-Terpineol is used as a fragrance ingredient in perfumes for its pleasant scent.
Used in Cosmetic Industry:
It is used in cosmetics for its pleasant scent and antimicrobial properties.
Used in Flavor Industry:
Alpha-terpineol is used as a synthetic flavoring agent to enhance the taste of various food products.
Used in Solvent Applications:
It is used as a solvent for extracting natural spices and as a solvent for acetate fibers.
Used in Antimicrobial Applications:
Alpha-terpineol is used as an antiseptic due to its strong and broad antimicrobial activity against fungi, bacteria, and viruses.
Used in Health and Wellness Industry:
It is used as an antioxidant, anti-inflammatory, and antihypernociception agent, providing health benefits.
Used in Disinfectant Production:
It is an important ingredient in pine oil disinfectants, contributing to their antimicrobial properties.
Used in Soap Production:
Alpha-terpineol is used as a fat denaturant for soap production, enhancing the soap's quality and effectiveness.
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.
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.
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
Preparation of α-terpineol and perillyl alcohol using zeolites beta
?erveny, Libor,Vysko?ilová, Eli?ka,Zítová, Kate?ina
, p. 4297 - 4310 (2021/07/26)
The preparation of α-terpineol by direct hydration of limonene catalyzed by zeolites beta was studied. The same catalyst was used to prepare perillyl alcohol by isomerization of β-pinene oxide in the presence of water. The aim was to optimize the reaction conditions to achieve high conversions of starting material and high selectivity to the desired products. In the case of limonene, it was found that the highest selectivity to α-terpineol was 88% with conversion of 36% under the conditions: 50?wt% of catalyst beta 25, 10% aqueous acetic acid (10?mL) (volume ratio limonene:H2O = 1:4.5), temperature 50?°C, after 24?h. In the case of β-pinene oxide, it was found that the highest selectivity to perillyl alcohol, which was 36% at total conversion, was obtained in the reaction under the following conditions: dimethyl?sulfoxide as solvent (volume ratio β-pinene oxide:DMSO = 1:5), catalyst beta 25 without calcination (15?wt%), demineralized water (molar ratio β-pinene oxide:H2O = 1:8), temperature 70?°C, 3?h. The present study shows that the studied reactions are suitable for the selective preparation of chosen compounds.
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.].
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.