2153-26-6

Basic information

• Product Name: TERPINYL FORMATE
• Synonyms: 3-Cyclohexene-1-methanol,.alpha.,.alpha.-4-trimethyl-,formate;alpha,alpha,4-trimethyl-3-cyclohexene-1-methanoformate;p-1-Menthen-8-ylformate;p-menth-1-en-8-ol,formate(mixedisomers);p-menth-1-en-8-ylformate;FEMA 3052;ALPHA TERPINYL FORMATE;TERPINYL FORMATE
• CAS NO: 2153-26-6
• Molecular Formula: C₁₁H₁₈O₂
• Molecular Weight: 182.26
• EINECS: 218-444-0
• Mol File: 2153-26-6.mol

Chemical Properties

• Boiling Point: 220 °C(lit.)
• Flash Point: 207 °F
• Appearance: /
• Density: 0.981 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0469mmHg at 25°C
• Refractive Index: n20/D 1.471(lit.)
• CAS DataBase Reference: TERPINYL FORMATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERPINYL FORMATE(2153-26-6)
• EPA Substance Registry System: TERPINYL FORMATE(2153-26-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: OT0220000
• Hazardous Substances Data: 2153-26-6(Hazardous Substances Data)

Usage

Uses

Used in Fragrance Industry:
TERPINYL FORMATE is used as a fragrance ingredient for its distinct floral and citrus scent. Its ability to provide a pleasant aroma makes it a valuable addition to the formulation of various perfumes, colognes, and other scented products.
Used in Flavor Industry:
TERPINYL FORMATE is used as a flavoring agent for its unique bitter taste at high levels and dry, fruity taste at lower levels. It is commonly utilized in the food and beverage industry to enhance the taste of various products, such as candies, beverages, and other confectionery items.
Used in Essential Oils:
TERPINYL FORMATE is used as a component in essential oils, particularly in Ceylon cardamom essential oil. Its presence contributes to the overall aroma and therapeutic properties of the essential oil, making it a sought-after ingredient in the production of aromatherapy products and natural remedies.
Used in Cosmetics and Personal Care Products:
TERPINYL FORMATE is used as an additive in cosmetics and personal care products, such as lotions, creams, and shampoos, for its pleasant scent and potential skin benefits. Its inclusion can enhance the sensory experience of using these products and provide a refreshing, uplifting effect for the user.

Preparation

By cold formylation of terpineol, using formic-acetic anhydride (Arctander, 1969). Uses: In public use before the 1920s. Use in fragrances in the USA amounts to approximately 10001b/yr.

Synthesis

May be produced from d-α-terpineol and formic acetic anhydride; the racemic α-terpineol is also obtained by an analogous synthesis.

InChI:InChI=1/C11H18O2/c1-9-4-6-10(7-5-9)11(2,3)13-8-12/h4,8,10H,5-7H2,1-3H3/t10-/m1/s1

Upstream product

• 7785-70-8 (+)-α-pinene 
• 64-18-6 formic acid 
• 39864-10-3 α-terpinyl chloride 
• 2258-42-6 formyl acetic anhydride 
• 138-86-3 limonene. 
• 98-55-5 terpineol 
• 463-73-0 carboxy chlorine 
• 1558-67-4 formic anhydride 

Downstream Products

• 38235-58-4 trans-sobrerol 

Relevant articles and documents

Discovery of a novel series of α-terpineol derivatives as promising anti-asthmatic agents: Their design, synthesis, and biological evaluation

A series of novel α-terpineol derivatives were designed and synthesized through structural derivatization of the tertiary hydroxyl moiety or reduction of the double bond. Of the resulting compounds, eight compounds enhanced relaxation of airway smooth muscle (ASM) compared to the α-terpineol precursor, and four compounds (4a, 4d, 4e, and 4i)were superior or comparable to aminophylline at a concentration of 0.75 mmol/L. Assays for 3′-5′-Cyclic adenosine monophpsphate (cAMP) activation revealed that some representative α-terpineol derivatives in this series were capable of upregulating the level of cAMP in ASM cells. Further in vivo investigation using the asthmatic rat model, illustrated that treatment with the compounds 4a and 4e resulted in significantly lowered lung resistance (RL) and enhanced dynamic lung compliance (Cldyn), two important parameters for lung fuction. Moreover, treatment with 4e downregulated the levels of both IL-4 and IL-17. Due to its several favorable physiological functions, including ASM relaxation activity, cAMP activation capability, and in vivo anti-asthmatic efficacy, 4e is a promising remedy for bronchial asthma, meriting extensive development.

Α- [...] enol derivative and its preparation method and application

The invention discloses alpha-terpineol derivatives, the structure of which is shown as the formula (II), wherein R or H is C1-C5 alkyl. The alpha-terpineol derivatives can be obtained by performing esterification reaction on a raw material alpha-terpineol with acid or acid anhydride at the temperature of 18-30DEG C under the action of 4-methylbenzenesulfonyl chloride. The invention further discloses applications of the alpha-terpineol derivatives in preparing antiasthmatic drugs, carboxylic ester prodrug formed by introducing carboxylic ester on the hydroxyl of the alpha-terpineol derivatives can be slowly hydrolyzed in a human body to release parent drug and further prolong the curative effect and the acting time, in addition the bioavailability can be improved, and the antiasthma activity can be further enhanced.

ANTIMICROBIAL COMPOSITION COMPRISING THYMOL AND A TERPINYL DERIVATIVE

The present invention relates to an antimicrobial composition and a method for disinfection involving the antimicrobial composition. It particularly relates to an antimicrobial composition for personal cleaning, oral care or hard surface cleaning applications. It was found that compositions comprising thymol, selected terpinyl derivatives and a carrier provide synergistic antimicrobial action. In a preferred aspect the composition also comprises 1 to 80 %-wt of surfactant.

P-Toluenesulfonyl chloride as a new and effective catalyst for acetylation and formylation of hydroxyl compounds under mild conditions

The catalytic application of p-toluenesulfonyl chloride for efficient acetylation of various types of alcohols and phenols with acetic anhydride in solvent-free conditions is reported. Also structurally diverse alcohols were formylated using formic acid based on the use of catalytic amount of p-toluenesulfonyl chloride under solvent-free condition. The reactions were carried out in short reaction time and in good to excellent yields at room temperature.

SOLVOLYTIC DISPLACEMENT OF ALKYL HALIDES BY METAL SALTS. PREPARATIVE PROCEDURES FOR ALLYL-, BENZYL- AND TERTIARY ALKYL-OXY DERIVATIVES USING THE ZINC SALTS

Reaction of allylic, benzylic and tertiary alkyl halides with zinc oxide in protic solvents leads to the formation of the corresponding alcohols, ethers and esters in good yields.The scope and limitations of this reaction have been examined.The possible involvement of ion quadruplets in the reaction is suggested.