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
Hydration of alpha-Pinene to obtain alpha-terpineol, using an ionic liquid as solvent, which is synthesized from a tertiary amine and an inorganic acid
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Paragraph 0016-0020, (2021/06/11)
An ionic liquid as a solvent in the hydration reaction of α-pinene to α-terpineol. The ionic liquid is obtained from the reaction of an amine and an inorganic acid. The use of the ionic liquid as solvent favors the selectivity towards the formation of α-terpineol and once the reaction product has been brought to room temperature, the organic phase can be physically separated from the inorganic one by decantation. The inorganic phase contains the ionic liquid, water and reaction catalyst and can be directly reused for a new reaction batch.
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.
