13601-88-2

Usage

Physical state

Pale yellow solid at room temperature

Aromaticity

Highly aromatic compound with a strong odor

Uses

Raw material in the production of dyes, pigments, and pharmaceuticals; reagent in organic synthesis, especially in the preparation of various aromatic compounds

Toxicity

Moderately toxic, can irritate skin, eyes, and respiratory system

Handling precautions

Should be handled with caution

Presence in consumer products

Not widely used, may be found in industrial and laboratory settings.

InChI:InChI=1S/C20H28O/c1-14(2)15-6-8-17-16(12-15)7-9-18-19(3,13-21)10-5-11-20(17,18)4/h6,8,12-14,18H,5,7,9-11H2,1-4H3/t18?,19-,20?/m1/s1

Upstream product

• 3772-55-2 dehydroabietinol 
• 22478-66-6 dehydroabietic acid chloride 
• 666-84-2 abietinol 
• 79-54-9 levopimaric acid 
• 3513-69-7 methyl ester of levopimaric acid 
• 514-10-3 abietic acid 
• 127-25-3 methyl abietate 
• 1228-43-9 Dehydroabietol 
• 28119-06-4 (1R,4aS)-7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-1-ylmethyl-cyanamide 
• 850380-03-9 Dehydroabietylamine 
• 911316-54-6 dehydroabietic acid 
• 1446-61-3 leelamine 
• 1235-74-1 Methyl dehydroabietate 
• 1740-19-8 dehydroabietic acid 

Downstream Products

• 22478-65-5 18-norabieta-8,11,13-trien-4-ol 
• 33980-70-0 4-hydroxy-19-nor-dehydroabietane 
• 3772-55-2 dehydroabietinol 
• 67119-95-3 (5S,10S)-abieta-9,11,13-trien-14-ol 
• 514-62-5 ferruginol 
• 79328-77-1 (1R,4aS)-1-[(E)-2-(4-Chloro-benzenesulfonyl)-vinyl]-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene 
• 105037-83-0 7-keto-15-hydroxydehydroabietane 

Relevant academic research and scientific papers

Bispericyclic Diels–Alder Dimerization of ortho-Quinols in Natural Product (Bio)Synthesis: Bioinspired Chemical 6-Step Synthesis of (+)-Maytenone

Many natural products of plant or microbial origins are derived from enzymatic dearomative oxygenation of 2-alkylphenolic precursors into 6-alkyl-6-hydroxycyclohexa-2,4-dienones. These so-called ortho-quinols cyclodimerize via a remarkably selective bispericyclic Diels–Alder reaction. Whether or not the intervention of catalytic or dirigent proteins is involved during this final step of the biosynthesis of these natural products, this cyclodimerization of ortho-quinols can be chemically reproduced in the laboratory with the same strict level of site-specific regioselectivity and stereoselectivity. This unique yet unified process, which finds its rationale in the inherent chemical reactivity of those ortho-quinols, is illustrated herein by an efficient and bioinspired first chemical synthesis of one of the most structurally complex and synthetically challenging examples of such natural cyclodimers, the bisditerpenoid (+)-maytenone.

Synthesis of bodinieric acids A and B, both C-18 and C-19-functionalized abietane diterpenoids: DFT study of the key aldol reaction

The first synthesis of C-18- and C-19-bifunctionalized abietane diterpenoids, bodinieric (or callicapoic) acids, via an aldol reaction has been developed. This key aldol reaction was very sensitive to steric hindrance. This fact has been studied by deuterium exchange experiments and DFT methods. Optimization of this reaction led to the synthesis of anti-inflammatory bodinieric acids A and B, starting from abietic acid.

NEW DERIVATES OF DHAA WITH ELECTROSTATIC TUNING

Dehydroabietic acid derivatives according to Formula Ia or Formula Ib and all stereoisomers thereof, having a linker chain A of 1 to 10 atoms selected from carbon, nitrogen and oxygen to a group X capable of being negatively charged at a physiological pH and covalently attached to the linker chain A, selected from carboxyl, sulfate, sulfonate and phosphate groups. The Dehydroabietic acid derivatives are useful for therapeutic treatment of hyperexcitablity diseases

Mild Ring-Opening 1,3-Hydroborations of Non-Activated Cyclopropanes

The Brown hydroboration reaction, first reported in 1957, is the addition of B?H across an olefin in an anti-Markovnikov fashion. Here, we solved a long-standing problem on mild 1,3-hydroborations of non-activated cyclopropanes. A three-component system including cyclopropanes, boron halides, and hydrosilanes has been developed for borylative ring-opening of cyclopropanes following the anti-Markovnikov rule, under mild reaction conditions. Density functional theory (M06-2X) calculations show that the preferred pathway involves a cationic boron intermediate which is quenched by hydride transfer from the silane.

Synthesis and biological evaluation of dehydroabietic acid derivatives

A series of C18-oxygenated derivatives of dehydroabietic acid were synthesized from commercial abietic acid and evaluated for their cytotoxic, antimycotic, and antiviral activities.

Synthesis of 12-deoxyroyleanone, cryptoquinone, 11,14-dihydroxy-8,11,13- abietatrien-7-one, and related derivatives from dehydroabietic acid

Naturally occurring abietane quinones and hydroquinone, namely, 12-deoxyroyleanone (1a), cryptoquinone (4a), and 11,14-dihydroxyabieta-8,11,13- trien-7-one (5a), together with the epimers of tryptoquinones D (2) and F (3), were first synthesized from dehydroabietic acid (6).

Structural effects on the bioactivity of dehydroabietic acid derivatives

The synthesis and the evaluation of the antimicrobial activity against a filamentous fungus, yeasts and bacteria of 15 hydrophenanthrene compounds derived from dehydroabietic acid, bearing different functional groups and different stereochemistry of the A/B ring junction are disclosed. The results obtained showed how their activity is dependent of the functionality at C-18, which can be increased by deisopropylation or introduction of other groups into the molecule. While the filamentous fungus tested is sensitive to almost all of the compounds under study, the aldehyde function showed to be of major importance to the inhibition of yeast. Alcohols and aldehyde C-18 derivatives also inhibit the growth of a Gram-positive bacteria, whereas Gram-negative are not sensitive.

Diels-Alder adducts of C-60 and resin acid derivatives: Synthesis, electrochemical and fluorescence properties

New, stable and quite soluble [2+4] mono-adducts of [60]fullerene with levopimaric acid derivatives were synthesised in high yields. These adducts were also obtained directly from pine rosin. Electrochemical behaviour and fluorescence properties, including the observation of thermal delayed fluorescence, are reported.

Preparation of potential anti-inflammatory agents from dehydroabietic acid

Methyl 16-nor-16-carboxydehydroabietate (22), 16-nor-16- carboxydehydroabietinol acetate (23), methyl 7-keto-16-nor-16- carboxydehydroabietate (29), 16-nor-16-carboxydehydroabietic acid (30), 16- nor-16-carboxydehydroabietinol (31), 7-keto-16-nor-16-carboxydehydroabietic acid (32), methyl 7-hydroxy-16-nor-16-carboxydehydroabietate (33), and 7- hydroxy-16-nor-16-carboxydehydroabietic acid (34) were prepared from dehydroabietic acid. Only 22 and 32 had weak anti-inflammatory activity.

Conversion of Abietic Acid into Analogues of Ambergris Odorants

The conversion of methyl abietate (16) into (42) and (43), analogues of the known amber odorants (1) and (2), is reported.