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SMB00089

Sigma-Aldrich

Dehydroabietic acid

≥90% (LC/MS-ELSD)

Sinónimos:

Abieta-8,11,13-trien-18-oic acid, Dehydroabietate

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About This Item

Fórmula empírica (notación de Hill):
C20H28O2
Número de CAS:
1740-19-8
Peso molecular:
300.44
EC Number:
217-102-8
MDL number:
MFCD09839012
UNSPSC Code:
12352205
PubChem Substance ID:
329824767
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

Categorías relacionadas

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
GHS06,GHS09

signalword

Danger

hcodes

H301,H410

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_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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
Teris A van Beek et al.
Journal of natural products, 70(2), 154-159 (2007-02-24)
Dehydroabietic acid (DHA) (1) is one of the main compounds in Scots pine wood responsible for aquatic and microbial toxicity. The degradation of 1 by Trametes versicolor and Phlebiopsis gigantea in liquid stationary cultures was followed by HPLC-DAD-ELSD. Both fungi
Estefanía Suárez-Vidal et al.
American journal of botany, 108(1), 102-112 (2021-01-30)
Persistence of tree populations in the face of global change relies on their capacity to respond to biotic and abiotic stressors through plastic or adaptive changes. Genetic adaptation will depend on the additive genetic variation within populations and the heritability
Yong-Mei Cui et al.
Bioorganic & medicinal chemistry letters, 18(19), 5201-5205 (2008-09-16)
A series of dehydroabietic acid (DHAA, 2) derivatives was synthesized and evaluated as BK channel openers in an assay system of CHO-K1 cells expressing hBKalpha channels. Systematic modifications of the peripheral functionality of ring C of DHAA showed that the
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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