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Dehydroabietic acid

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Dehydroabietic acid 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
  • 1-Phenanthrenecarboxylicacid, 1,2,3,4,4a,9,10,10a-octahydro-1,4a-diMethyl-7-(1-Methylethyl)-,(1R,4aS,10aR)-
  • [1R-(1alpha,4abeta,10aalpha)]-1,2,3,4,4a,9,10,10a-octahydro-7-isopropyl-1,4a-dimethylphenanthren-1-carboxylic acid
CAS:
1740-19-8
MF:
C20H28O2
MW:
300.44
EINECS:
217-102-8
Mol File:
1740-19-8.mol
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Dehydroabietic acid Chemical Properties

Melting point:
174-176℃
Boiling point:
394.13°C (rough estimate)
Density 
1.058
refractive index 
1.5404 (estimate)
storage temp. 
Sealed in dry,Store in freezer, under -20°C
solubility 
DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 10 mg/ml
form 
A solid
pka
4.66±0.40(Predicted)
color 
White to yellow
InChIKey
NFWKVWVWBFBAOV-UHFFFAOYSA-N
LogP
6.120 (est)
EPA Substance Registry System
Dehydroabietic acid (1740-19-8)
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Safety Information

Hazard Codes 
T,N
Risk Statements 
25-50
Safety Statements 
45-61
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
1
HS Code 
29161900
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Dehydroabietic acid Usage And Synthesis

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 spectroscopy
to 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.

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