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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
Número CE:
217-102-8
Número MDL:
MFCD09839012
Código UNSPSC:
12352205
ID de la sustancia en PubChem:
329824767
NACRES:
NA.25

Análisis

≥90% (LC/MS-ELSD)

formulario

solid

aplicaciones

metabolomics
vitamins, nutraceuticals, and natural products

temp. de almacenamiento

−20°C

cadena 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

Clave InChI

NFWKVWVWBFBAOV-MISYRCLQSA-N

Categorías relacionadas

Descripción general

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).

Aplicación

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

Acciones bioquímicas o 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

Palabra de señalización

Danger

Frases de peligro

H301,H410

Consejos de prudencia

P273 - P301 + P310 + P330

Clasificaciones de peligro

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

Código de clase de almacenamiento

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

Clase de riesgo para el agua (WGK)

WGK 1

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°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
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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