631-71-0

Basic information

• Product Name: ABIETIC ACID ETHYL ESTER
• Synonyms: ETHYL ROSINATE;ETHYL ABIETATE;ABIETIC ACID ETHYL ESTER;ROSIN ACID ETHYL ESTER;ABIETIC ACID ETHYL ESTER 70.0+%;1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,4b,5,6,10,10a-decahydro-1,4a-dimethyl-7-(1-methylethyl)-, ethyl ester, (1R,4aR,4bR,10aR)-;(1R)-1,2,3,4,4a,4bα,5,6,10,10aα-Decahydro-1,4aβ-dimethyl-7-isopropyl-1α-phenanthrenecarboxylic acid ethyl ester;(1R)-1,2,3,4,4aα,4bα,5,6,10,10aα-Decahydro-1,4aβ-dimethyl-7-(1-methylethyl)-1α-phenanthrenecarboxylic acid ethyl ester
• CAS NO: 631-71-0
• Molecular Formula: C₂₂H₃₄O₂
• Molecular Weight: 330.5
• EINECS: 211-166-0
• Product Categories: Biochemistry;Terpenes;Terpenes (Others)
• Mol File: 631-71-0.mol

Chemical Properties

• Boiling Point: 417.9 ºC at 760 mmHg
• Flash Point: 178°C
• Appearance: /
• Density: 1,03 g/cm3
• Vapor Pressure: 3.43E-07mmHg at 25°C
• Refractive Index: 1.5270-1.5290
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: ABIETIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: ABIETIC ACID ETHYL ESTER(631-71-0)
• EPA Substance Registry System: ABIETIC ACID ETHYL ESTER(631-71-0)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• Hazardous Substances Data: 631-71-0(Hazardous Substances Data)

Usage

Uses

Used in Perfumery and Cosmetics Industry:
ABIETIC ACID ETHYL ESTER is used as a flavoring and fragrance agent for its sweet pine-like odor, adding a pleasant scent to perfumes and cosmetic products.
Used in Adhesives, Printing Inks, and Coatings Industry:
ABIETIC ACID ETHYL ESTER is utilized in the production of adhesives, printing inks, and coatings due to its chemical properties that enhance the performance and quality of these products.
Used in Pharmaceutical and Personal Care Products:
ABIETIC ACID ETHYL ESTER has been studied for its potential antimicrobial and antifungal properties, making it a promising candidate for use in pharmaceuticals and personal care products. However, further research is needed to fully understand its therapeutic potential and safety profile.

InChI:InChI=1/C22H34O2/c1-6-24-20(23)22(5)13-7-12-21(4)18-10-8-16(15(2)3)14-17(18)9-11-19(21)22/h9,14-15,18-19H,6-8,10-13H2,1-5H3/t18-,19+,21+,22+/m0/s1

Upstream product

• 64-67-5 diethyl sulfate 
• 514-10-3 abietic acid 
• 64-17-5 ethanol 
• 75-00-3 chloroethane 
• 56151-64-5 7,13-Abietadien-18-oic acid chloride 
• 75-03-6 ethyl iodide 
• 74-96-4 ethyl bromide 
• 14351-66-7 abietic acid sodium salt 
• 19897-44-0 7,13-Abietadien-18-oic acid anhydride 

Downstream Products

• 24563-96-0 1-hydroxymethyl-abietane p-methylbenzenesulfonate 
• 666-84-2 abietinol 

Relevant articles and documents

Design and synthesis of tricyclic terpenoid derivatives as novel PTP1B inhibitors with improved pharmacological property and in vivo antihyperglycaemic efficacy

Overexpression of protein tyrosine phosphatase 1B (PTP1B) induces insulin resistance in various basic and clinical research. In our previous work, a synthetic oleanolic acid (OA) derivative C10a with PTP1B inhibitory activity has been reported. However, C10a has some pharmacological defects and cytotoxicity. Herein, a structure-based drug design approach was used based on the structure of C10a to elaborate the smaller tricyclic core. A series of tricyclic derivatives were synthesised and the compounds 15, 28 and 34 exhibited the most PTP1B enzymatic inhibitory potency. In the insulin-resistant human hepatoma HepG2 cells, compound 25 with the moderate PTP1B inhibition and preferable pharmaceutical properties can significantly increase insulin-stimulated glucose uptake and showed the insulin resistance ameliorating effect. Moreover, 25 showed the improved in vivo antihyperglycaemic potential in the nicotinamide–streptozotocin-induced T2D. Our study demonstrated that these tricyclic derivatives with improved molecular architectures and antihyperglycaemic activity could be developed in the treatment of T2D.

Preparation method of 15-hydroxyl dehydrogenated abietane and intermediate of 15-hydroxyl dehydrogenated abietane

The invention discloses a preparation method of 15-hydroxyl dehydrogenated abietane and an intermediate of 15-hydroxyl dehydrogenated abietane. The preparation method comprises the following steps: converting a compound 1 into a compound 5, and converting the compound 5 into a compound 8. According to the method for preparing the compound 8, the problem that a product cannot be separated out of a glacial acetic acid solution because reaction impurities are remarkably increased when the feeding quantity is increased at the hydrogen bromide addition step in the existing synthesis route is solved through continuous screening of a process route. Furthermore, the method provided by the invention is high in yield at each step, easy to amplify and suitable for industrialized large-scale production. (The formula is as shown in the description.).

8. 11, 13 - Lohans Pinaceae - 13 - ol and intermediate preparation method (by machine translation)

The present invention discloses a process for preparing compound 9 shown 8, 11, 13 - Lohans Pinaceae - 13 - alcohol, or its pharmaceutically acceptable salt, or its solvate of the method, the method comprises the following steps: h, in the presence of oxidizing agent and acid, in order to compound 8 as raw material preparation to obtain compound 9; wherein oxidizing agent selected from hydrogen peroxide or over-tertiary butyl alcohol, acid selected from H2 SO4 , Toluenesulfonates. Process for making a compound of the present invention 9 of the method, the method is simple, high yield, easy to enlarge, and is suitable for industrial large-scale production. (by machine translation)

Rosin acid derivatives

The invention belongs to the technical field of chemical pharmacy, and particularly discloses a preparation method for an abietic acid derivative. Abietic acid 1 is dissolved in solvent, alkali is added, halogenated hydrocarbon is added, and then an intermediate 2 is obtained; the intermediate 2 is dissolved in solvent, lithium aluminum hydride is added, the pH is regulated to 6 through diluted hydrochloric acid, and then an intermediate 3 is obtained; the intermediate 3 is dissolved in solvent, paratoluensulfonyl chloride is added, and then an intermediate 4 is obtained; the intermediate 4 is dissolved in solvent, NaI and Zn are added, and then an intermediate 5 is obtained; the intermediate 5 is dissolved in solvent, hydrogen bromide is added, washing is performed through frozen glacial acetic acid, and then an intermediate 6 is obtained; the intermediate 6 is dissolved in solvent, alkali is added, diluted hydrochloric acid is added to regulate the PH to 2-3, and then an intermediate 7 is obtained; the intermediate 7 is dissolved in solvent, selenium dioxide is added, and a product 8 is obtained. According to the preparation method of the abietic acid derivative, the yield is high; particularly, Huang-Minlon reduction reaction needing high temperature is avoided, so that the requirement for reaction conditions is low; in addition, the product purity is greatly improved.

Anti-inflammatory activity of heterocyclic systems using abietic acid as starting material

A series of pyridines, pyrimidinone, oxazinones, and their derivatives were synthesized as anti-inflammatory agents using abietic acid (7-isopropyl-1,4a- dimethyl-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthrene-1-carboxylic acid) as the starting material. The arylidiene derivative was treated with cyanothioacetamide to give cyano pyridine-thione, which was reacted with ethyl chloroacetate to yield the corresponding cyano ester. The ester was hydrolysed to the sodium salt, which was reacted with acetic anhydride to afford 2-methyloxazinone, which was treated with ammonium acetate to afford 2-methylpyrimidinone followed by methylation with methyl iodide to yield 2,3-dimethyl- pyrimidinone. In addition, the oxazinone derivative was reacted with aniline or hydrazine hydrate to give 3-phenyl- or 3-aminopyrimidinones. The latter reacted with thiophene-2-carboxaldehyde or phenylisothiocyanate to afford Schiff's bases or thiosemicarbazide derivatives. The pharmacological screening showed that many of these compounds have good anti-inflammatory activity comparable to Prednisolone as reference drug.

Diterpenoid carboxylic acid anhydrides of the abietane, pimarane, and isopimarane series

Methods were developed for preparation of diterpenoid carboxylic acid anhydrides of the abietane, pimarane, and isopimarane series, the corresponding mixed anhydrides, and mixed anhydrides derived from resin acids and organic or inorganic acids. The resulting anhydrides sharply differ from the parent acids in physical properties; their thermal reactions and isomerizations and the rates of formation and hydrolysis were studied. The data obtained were used to develop new procedures for separation of anhydride mixtures into pure components. Reactions of abietic anhydride with some nucleophilic reagents gave the corresponding esters, ketones, amides, etc. Commercial samples of pine wood resins (gum rosin and tallic rosin) were shown to contain a small amount (0.2%) of diterpenoid anhydride mixtures.

Phytoalexin-like Activity of Abietic Acid and Its Derivatives

Abietic acid and some of its derivatives, not known to be naturally occurring phytoalexins, were examined for their ability to promote H+ conductance across membranes and to inhibit growth of two fungal species-Aphanomyces euteiches and Fusarium moniliforme.These results were compared with those of phaseollin, at phytoalexin isolated from kidney beans.Ion leakage and fungal growth inhibition were shown to be a function of structure, results that suggest that pterocarpan phytoalexin activity requires the presence of a polar, protic functional group situated at the end of a large, rigid hydrophobic moiety.Log P values for phaseollin, abietic acid, and some derivatives of abietic acid were also determined. Keywords: Abietic acid; H+ leakage; antifungal activity; log P; phaseollin