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SMB00089

Sigma-Aldrich

Dehydroabietic acid

≥90% (LC/MS-ELSD)

Sinônimo(s):

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

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About This Item

Fórmula empírica (Notação de Hill):
C20H28O2
Número CAS:
1740-19-8
Peso molecular:
300.44
Número CE:
217-102-8
Número MDL:
MFCD09839012
Código UNSPSC:
12352205
ID de substância PubChem:
329824767
NACRES:
NA.25

Ensaio

≥90% (LC/MS-ELSD)

forma

solid

aplicação(ões)

metabolomics
vitamins, nutraceuticals, and natural products

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

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

chave InChI

NFWKVWVWBFBAOV-MISYRCLQSA-N

Categorias relacionadas

Descrição geral

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).

Aplicação

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

Ações bioquímicas/fisiológicas

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.

Pictogramas

Skull and crossbonesEnvironment
GHS06,GHS09

Palavra indicadora

Danger

Frases de perigo

H301,H410

Declarações de precaução

P273 - P301 + P310 + P330

Classificações de perigo

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

Código de classe de armazenamento

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de risco de água (WGK)

WGK 1

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Certificados de análise (COA)

Busque Certificados de análise (COA) digitando o Número do Lote do produto. Os números de lote e remessa podem ser encontrados no rótulo de um produto após a palavra “Lot” ou “Batch”.

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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
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
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
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
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
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