1231-75-0

Usage

Uses

Used in Pharmaceutical Industry:
(+)-Dehydroabietic acid is used as a pharmaceutical compound for its potential anti-inflammatory, antioxidant, and antimicrobial properties. Its ability to modulate various biological pathways and exhibit therapeutic effects makes it a valuable asset in the development of new drugs and treatments.
Used in Cosmetics Industry:
(+)-Dehydroabietic acid is used as an ingredient in cosmetics for its potential skin health benefits. Its anti-inflammatory and antioxidant properties can contribute to the development of skincare products that promote healthy and radiant skin.
Used in Agriculture Industry:
(+)-Dehydroabietic acid is used in agriculture for its ability to enhance plant growth and protect against pathogens. Its potential applications in this industry include the development of biopesticides, plant growth regulators, and other agricultural products that can improve crop yield and resistance to diseases.
Used in Adhesives, Solvents, and Inks Industry:
(+)-Dehydroabietic acid, as a primary constituent of rosin, is used in the production of adhesives, solvents, and inks. Its natural origin and versatile properties make it a valuable component in these industries, contributing to the development of eco-friendly and high-performance products.

Synthetic route

Δ6-6-hydroxy-5βH-dehydroabietic acid (18-6)-lactone (74383-48-5) → 6-hydroxy-5βH-abieta-6,8,11,13-tetraen-18-oic acid (1231-75-0) + 6β-hydroxy-5βH-abieta-8,11,13-trien-18-oic acid 18,6β-lactone (74430-73-2) + 6α-hydroxy-5βH-abieta-8,11,13-trien-18-oic acid 18,6α-lactone (74383-49-6)

Conditions	Yield
With hydrogen; platinum(IV) oxide In acetic acid under 760 Torr; for 1.66667h; Ambient temperature; Title compound not separated from byproducts;	A n/a B 0.5% C 30%
With hydrogen; platinum(IV) oxide In acetic acid under 760 Torr; for 1.66667h; Ambient temperature;	A n/a B 0.5% C 30%

methyl (1R,4aS,10aR)-1,2,3,4,4a,10a-hexahydro-1,4a-dimethyl-7-(1-methylethyl)phenanthrene-1-carboxylate (18492-76-7) → 6-hydroxy-5βH-abieta-6,8,11,13-tetraen-18-oic acid (1231-75-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) perbenzoic acid, 2.) p-TsOH / 1.) CHCl3, RT, 24 h, 2.) toluene, reflux, 3 h 2: H2 / PtO2 / acetic acid / 1.67 h / 760 Torr / Ambient temperature View Scheme

6-hydroxy-5βH-abieta-6,8,11,13-tetraen-18-oic acid (1231-75-0) → Δ1-exo-Dehydroabietan

Conditions	Yield
With pyridine; lead(IV) acetate In benzene

Upstream product

• 18492-76-7 methyl (1R,4aS,10aR)-1,2,3,4,4a,10a-hexahydro-1,4a-dimethyl-7-(1-methylethyl)phenanthrene-1-carboxylate 
• 25017-78-1 3-cyano-2-cyclohexenone 
• 74383-48-5 Δ⁶-6-hydroxy-5βH-dehydroabietic acid (18-6)-lactone 

Relevant academic research and scientific papers

Oxonitriles: Multicomponent Grignard addition-alkylations

Three at a time: Sequential carbonyl addition, chelation-controlled conjugate addition, and alkylation triggers the multicomponent assembly of diverse nitriles. The chelation-controlled conjugate addition-alkylation installs three new stereocenters (see scheme), thereby generating substituted nitriles that are ideal terpenoid precursors as illustrated in the synthesis of epi-dehydroabietic acid.

The C(1)-C(10) Bond Cleavage and B Ring Aromatization of Some 6-Hydrpoxy-5βH-abieta-6,8,11,13-tetraen-18-oic Acid 18,6-Lactones

Fusion of 6-hydroxy-5βH-abieta-6,8,11,13-tetraen-18-oic acid 18,6-lactone (2) with potassium hydrogensulfate at 220 deg C afforded bisfuran-3-yl)propyl> ether (12) in 37percent yield, together with two minor products in 12percent yield: 2,3-dihydro-7-isopropyl-3,4-dimethyl-3-propylnaphthofuran-2-one and 3-allyl-2,3-dihydro-7-isopropyl-3,4-dimethylnaphthofuran-2-one.Treatment of 12 with p-toluenesulfonic acid at 160 deg C gave 2,3-dihydro-7-isopropyl-3,4-dimethyl-3-(3-tosyloxypropyl)naphthofuran-2-one, which was converted into 2,3-dihydro-3-(3-hydroxypropyl)-7-isopropyl-3,4-dimethylnaphthofuran-2-one (16).The alcohol 16 was further characterized as its acetate (17).After several attempts, the above C(1)-C(10) bond cleavage and B ring aromatization reaction were improved by use of concentrated sulfuric acid in refluxing acetic acid.Under this conditions, 2 gave 17 in 47percent yield.Hydrolysis of 17 with hydrochloric acid afforded 16.Subsequently, 12-hydroxy-, 12-methoxy-, 12-acetoxy-, and 12-nitro-6-hydroxy-5βH-abieta-6,8,11,13-tetraen-18-oic acid 18,6-lactones were each refluxed with concentrated sulfuric acid in acetic acid to give 6-hydroxy-, 6-methoxy-, 6-acetoxy-, and 6-nitro-3-(3-acetoxypropyl)-2,3-dihydro-7-isopropyl-3,4-dimethylnaphthofuran-2-ones, respectively.From the present study, the 12-acetoxy derivative seems to be a suitable intermediate for the synthesis of coleon A.