1740-19-8

Basic information

• Product Name: DEHYDROABIETIC ACID
• Synonyms: [1theta-(1alpha,4abeta,10aalpha)]--methylethyl);13-isopropylpodocarpa-8,11,13-trien-15-oicacid;13-trien-15-oicacid,13-isopropyl-podocarpa-11;1-phenanthrenecarboxylicacid,1,2,3,4,4a,9,10,10a-octahydro-1,4a-dimethyl-7-(1;dehydro-abieticaci;DEHYDROABIETIC ACID;[1R-(1alpha,4abeta,10aalpha)]-1,2,3,4,4a,9,10,10a-octahydro-7-isopropyl-1,4a-dimethylphenanthren-1-carboxylic acid;PODOCARPA-8,11,13-TRIEN-15-OICACID,13-ISOPROPYL-
• CAS NO: 1740-19-8
• Molecular Formula: C₂₀H₂₈O₂
• Molecular Weight: 300.44
• EINECS: 217-102-8
• Mol File: 1740-19-8.mol
• Article Data: 14

Chemical Properties

• Melting Point: 174-176℃
• Boiling Point: 394.13°C (rough estimate)
• Flash Point: 202.504 °C
• Appearance: /
• Density: 1.058
• Vapor Pressure: 5.53E-08mmHg at 25°C
• Refractive Index: 1.5404 (estimate)
• Storage Temp.: ?20°C
• PKA: 4.66±0.40(Predicted)
• CAS DataBase Reference: DEHYDROABIETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: DEHYDROABIETIC ACID(1740-19-8)
• EPA Substance Registry System: DEHYDROABIETIC ACID(1740-19-8)

Safety Data

• Hazard Codes: T,N
• Statements: 25-50
• Safety Statements: 45-61
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 1
• Hazardous Substances Data: 1740-19-8(Hazardous Substances Data)

Usage

Chemical Properties

White Solid or Colorless needle crystal, Slightly soluble in water, soluble in methanol, ethanol, DMSO and other organic solvents. It is an abietane diterpenic resin acid that is obtained from Pinus resin.

Uses

Dehydroabietic Acid is a resin acid found commonly in rosin. Dehydroabietic Acid is used in rosin-type nucleating agent for polypropylene (PP). Dehydroabietic Acid is used commonly in the synthesis of surfactants, antioxidants and chiral catalysts.

Definition

ChEBI: Dehydroabietic acid is an abietane diterpenoid that is abieta-8,11,13-triene substituted at position 18 by a carboxy group. It has a role as a metabolite and an allergen. It is an abietane diterpenoid, a monocarboxylic acid and a carbotricyclic compound. It derives from an abietic acid. It is a conjugate acid of a dehydroabietate.

Application

Dehydroabietic acid (DHA or DAA) is a bioactive phytochemical, diterpenoid found in various Pinus species. It is a resin acid and a derivative of abietic acid (AA).Dehydroabietic acid has been used as a reference standard:to study the aging process of Pinus resins using Fourier-transform infrared spectroscopy (FTIR)to study the composition changes in Pinus genus with aging using Raman spectroscopy complemented with infrared spectroscopyto estimate resistance against biotic stress as proxy in chemical defenses in Pinus halepensis

Biochem/physiol Actions

Dehydroabietic acid (DHA) exerts various biological activities such as anti-cancer, anti-aging, antimicrobial, antiulcer, gastroprotective, and cytotoxic activities. It is a potent anti-inflammatory agent and a dual activator of peroxisome proliferator-activated receptors alpha and gamma (PPAR α/γ). DHA has an anti-aging effect and a sirtuin 1 (SIRT1) activating compound. It has antibacterial properties against multidrug-resistant strains. dehydroabietic acid and its derivatives have gastroprotective and cytotoxic effects.

InChI:InChI=1/C20H28O2/c1-13(2)14-6-8-16-15(12-14)7-9-17-19(16,3)10-5-11-20(17,4)18(21)22/h6,8,12-13,17H,5,7,9-11H2,1-4H3,(H,21,22)/t17-,19+,20+/m0/s1

Upstream product

• 25017-78-1 3-cyano-2-cyclohexenone 
• 471-77-2 neoabietic acid 
• 37905-03-6 8-hydroxygeranyl acetate 
• 1527482-56-9 (1S,4aS,10aS)-7-isopropyl-1,4a-dimethyl-1-(2-methylprop-1-enyl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene 
• 1527482-54-7 1-isopropyl-3-((3E,7E)-4,8,10-trimethylundeca-3,7,9-trienyl)benzene 
• 51473-70-2 1-(m-isopropylphenyl)methanol 
• 5433-01-2 1-bromo-3-isopropylbenzene 
• 1527482-52-5 (2E,6E)-3,7,9-trimethyldeca-2,6,8-trienyl acetate 
• 37905-02-5 (2E,6E)-3,7-dimethyl-8-oxoocta-2,6-dien-1-yl acetate 
• 105-87-3 3,7-dimethyl-2E,6-octadien-1-yl acetate 
• 514-10-3 (?)-abietic acid 
• 1235-74-1 Methyl dehydroabietate 
• 7664-93-9 sulfuric acid 
• 33159-27-2 12-sulfodehydroabietic acid 

Downstream Products

• 1235-74-1 Methyl dehydroabietate 
• 5335-62-6 18-phenyl-abieta-8,11,13-trien-18-ol 

Relevant articles and documents

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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.

Late-stage C-H amination of abietane diterpenoids

This study aims at highlighting the synthetic versatility of the rhodium-catalyzed C-H amination reactions using iodine(iii) oxidants for the late-stage functionalization of natural products. Inter-and intramolecular nitrene insertions have been performed from various abietane diterpenoids, leading to the amination of the C-3, C-6, C-7, C-11 and C-15 positions. Ca. 20 aminated compounds have been isolated with yields of up to 86% and high levels of regio-, chemo-and stereoselectivities.

Syntheses of taiwaniaquinone F and taiwaniaquinol A via an unusual remote C-H functionalization

A protecting-group-free route to (-)-taiwaniaquinone F based on a ring contraction and subsequent aromatic oxidation of a sugiol derivative is reported. In addition, the first synthesis of (+)-taiwaniaquinol A is reported via short time exposure of (-)-taiwaniaquinone F to sunlight triggering a remote C-H functionalization. The hypothesis that the biogenesis of some methylenedioxy bridged natural products could proceed via similar nonenzymatic mechanisms is presented.