SMB00089
Dehydroabietic acid
≥90% (LC/MS-ELSD)
Synonym(s):
Abieta-8,11,13-trien-18-oic acid, Dehydroabietate
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About This Item
Empirical Formula (Hill Notation):
C20H28O2
CAS Number:
Molecular Weight:
300.44
NACRES:
NA.25
PubChem Substance ID:
UNSPSC Code:
12352205
EC Number:
217-102-8
MDL number:
Product Name
Dehydroabietic acid, ≥90% (LC/MS-ELSD)
InChI key
NFWKVWVWBFBAOV-MISYRCLQSA-N
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
SMILES string
CC(C)c1ccc2c(CC[C@H]3[C@@](C)(CCC[C@]23C)C(O)=O)c1
assay
≥90% (LC/MS-ELSD)
form
solid
application(s)
metabolomics
vitamins, nutraceuticals, and natural products
storage temp.
−20°C
Related Categories
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.
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).
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1
Storage Class
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
wgk
WGK 1
flash_point_f
Not applicable
flash_point_c
Not applicable
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Xianxing Jiang et al.
Organic letters, 11(1), 153-156 (2008-12-11)
A new class of dehydroabietic amine-substituted primary amine-thiourea bifunctional catalysts were designed and synthesized. The doubly stereocontrolled organocatalytic conjugate addition of a variety of heterocycles-bearing ketones to nitroalkenes was investigated for the first time, affording (S)- or (R)-gamma-nitro heteroaromatic ketones
Xin Wan et al.
Environmental pollution (Barking, Essex : 1987), 247, 216-228 (2019-01-25)
Biomass burning (BB) is one of the largest sources of carbonaceous aerosols with adverse impacts on air quality, visibility, health and climate. BB emits a few specific aromatic acids (p-hydroxybenzoic, vanillic, syringic and dehydroabietic acids) which have been widely used
Markers, Reactions, and Interactions during the Aging of Pinus Resin Assessed by Raman Spectroscopy.
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
Nor Fadhilah Kamaruzzaman et al.
Materials (Basel, Switzerland), 11(9) (2018-09-16)
Infectious disease caused by pathogenic bacteria continues to be the primary challenge to humanity. Antimicrobial resistance and microbial biofilm formation in part, lead to treatment failures. The formation of biofilms by nosocomial pathogens such as Staphylococcus aureus (S. aureus), Pseudomonas
Dehydroabietic acid, a diterpene, improves diabetes and hyperlipidemia in obese diabetic KK-Ay mice.
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.
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