80-27-3

Basic information

• Product Name: TERPINYL PROPIONATE
• Synonyms: 1-Methyl-1-(4-methyl-3-cyclohexen-1-yl)ethyl propionate;3-Cyclohexene-1-methanol, alpha,alpha,4-trimethyl-, propanoate;3-Cyclohexene-1-methanol,.alpha.,.alpha.,4-trimethyl-,propanoate;4-Terpinenyl ester of propanoic acid;alpha,alpha,4-trimethyl-3-cyclohexene-1-methanopropanoate;alpha-Terpinyl ester of propanoic acid;p-menth-1-en-8-ylpropionate;Terpenyl propionate
• CAS NO: 80-27-3
• Molecular Formula: C₁₃H₂₂O₂
• Molecular Weight: 228.33
• EINECS: 201-266-2
• Mol File: 80-27-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 240 °C(lit.)
• Flash Point: 71 °C
• Appearance: Colorless to slightly yellow liquid
• Density: 0.949 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0133mmHg at 25°C
• Refractive Index: n20/D 1.464(lit.)
• CAS DataBase Reference: TERPINYL PROPIONATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERPINYL PROPIONATE(80-27-3)
• EPA Substance Registry System: TERPINYL PROPIONATE(80-27-3)

Safety Data

• WGK Germany: 2
• Hazardous Substances Data: 80-27-3(Hazardous Substances Data)

Usage

Chemical Properties

Terpinyl propionate has a somewhat floral, lavender note with a bitter flavor

Occurrence

Reported found in citrus fruit and celery; also the racemic form (dl) has been identified in cardamom.

Preparation

By esterification of terpineols.

Taste threshold values

Taste characteristics at 20 ppm: sweet, green with tropical and fruity nuances.

InChI:InChI=1/C13H22O2/c1-5-12(14)15-13(3,4)11-8-6-10(2)7-9-11/h6,11H,5,7-9H2,1-4H3

Upstream product

• 98-55-5 terpineol 
• 123-62-6 propionic acid anhydride 
• 105-91-9 (Z)-3,7-dimethyl-2,6-octadien-1-yl propanoate 
• 138-86-3 limonene. 
• 39864-10-3 α-terpinyl chloride 
• 802294-64-0 propionic acid 

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.

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.