All Photos(1)

SMB00089

Sigma-Aldrich

Dehydroabietic acid

≥95% (LC/MS-ELSD)

Synonym(s):
Abieta-8,11,13-trien-18-oic acid, Dehydroabietate
Empirical Formula (Hill Notation):
C20H28O2
CAS Number:
Molecular Weight:
300.44
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.25

assay

≥95% (LC/MS-ELSD)

form

solid

storage temp.

−20°C

SMILES string

CC(C)c1ccc2c(CC[C@H]3[C@@](C)(CCC[C@]23C)C(O)=O)c1

InChI

1S/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-/m1/s1

InChI key

NFWKVWVWBFBAOV-MISYRCLQSA-N

General description

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).

Application

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.

Pictograms

Skull and crossbonesEnvironment

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Daryl J Smith et al.
Journal of bacteriology, 186(11), 3631-3639 (2004-05-20)
Diterpenoids are naturally occurring plant compounds which have pharmaceutical properties. We have sequenced a 10.4-kbp extension of the dit cluster in Pseudomonas abietaniphila BKME-9, containing genes involved in abietane diterpenoid biodegradation. The ditQ gene was found to encode a cytochrome
M Ruths et al.
Langmuir : the ACS journal of surfaces and colloids, 24(4), 1509-1516 (2007-12-19)
The effects of adhesion, contact area, and pressure on the lubricating properties of self-assembled monolayers on steel have been investigated with friction force microscopy. The adsorbed molecules were fatty acids with varying degrees of unsaturation (0-2 double bonds; stearic, oleic
Beatriz Sepúlveda et al.
Pharmacological research, 52(5), 429-437 (2005-08-30)
Dehydroabietic acid derivatives have been reported to display antisecretory and antipepsin effect in animal models. Some 19 dehydroabietic acid diterpenes were prepared and assessed for gastroprotective activity in the HCl/EtOH-induced gastric lesions in mice as well as for cytotoxicity in
Min-Sook Kang et al.
BioFactors (Oxford, England), 35(5), 442-448 (2009-09-16)
Terpenoids, which are contained in a large number of dietary and herbal plants, have many biological effects. In this study, the effects of dehydroabietic acid (DAA), a diterpene, on glucose and lipid metabolism were examined using obese diabetic KK-Ay mice.
Victoria Beltran et al.
Journal of natural products, 80(4), 854-863 (2017-03-31)
The resin extracted from the species of the Pinus genus (Pinaceae family) is a widely used material. Primarily, resins are made up of two types of diterpenoids: abietanes and pimaranes. Their composition changes with aging, affecting their chemical and physical

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