SMB00089
Dehydroabietic acid
≥90% (LC/MS-ELSD)
Sinónimos:
Abieta-8,11,13-trien-18-oic acid, Dehydroabietate
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Fórmula empírica (notación de Hill):
C20H28O2
Número CAS:
Peso molecular:
300.44
NACRES:
NA.25
PubChem Substance ID:
UNSPSC Code:
12352205
EC Number:
217-102-8
MDL number:
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≥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.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1
Clase de almacenamiento
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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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
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
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
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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