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SMB00089

Sigma-Aldrich

Dehydroabietic acid

≥90% (LC/MS-ELSD)

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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

≥90% (LC/MS-ELSD)

form

solid

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

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

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Dehydroabietic acid ≥90% (LC/MS-ELSD)

Sigma-Aldrich

SMB00089

Dehydroabietic acid

Betulinic acid ≥98% (HPLC)

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Arjunolic acid ≥95% (LC/MS-ELSD)

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Pomolic acid ≥90% (LC/MS-ELSD)

Sigma-Aldrich

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form

solid

form

powder

form

solid

form

solid

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

−20°C

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

6.1C - 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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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
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
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.
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
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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

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