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SMB00089

Sigma-Aldrich

Dehydroabietic acid

≥90% (LC/MS-ELSD)

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C20H28O2
Numero CAS:
1740-19-8
Peso molecolare:
300.44
Numero CE:
217-102-8
Numero MDL:
MFCD09839012
Codice UNSPSC:
12352205
ID PubChem:
329824767
NACRES:
NA.25

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Saggio

≥90% (LC/MS-ELSD)

Stato

solid

applicazioni

metabolomics
vitamins, nutraceuticals, and natural products

Temperatura di conservazione

−20°C

Stringa SMILE

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
NFWKVWVWBFBAOV-MISYRCLQSA-N

Categorie correlate

Descrizione generale

Dehydroabietic acid (DHA or DAA) is a bioactive phytochemical, diterpenoid found in various Pinus species.[1] It is a resin acid and a derivative of abietic acid (AA).[2]

Applicazioni

Dehydroabietic acid has been used as a reference standard:
  • to study the aging process of Pinus resins using Fourier-transform infrared spectroscopy (FTIR)[3]
  • to study the composition changes in Pinus genus with aging using Raman spectroscopy complemented with infrared spectroscopy[4]
  • to estimate resistance against biotic stress as proxy in chemical defenses in Pinus halepensis[5]

Azioni biochim/fisiol

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).[2] DHA has an anti-aging effect and a sirtuin 1 (SIRT1) activating compound.[1] It has antibacterial properties against multidrug-resistant strains.[6] dehydroabietic acid and its derivatives have gastroprotective and cytotoxic effects.[7]

Pittogrammi

Skull and crossbonesEnvironment
GHS06,GHS09

Avvertenze

Danger

Indicazioni di pericolo

H301,H410

Consigli di prudenza

P273 - P301 + P310 + P330

Classi di pericolo

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

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 1

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

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Certificati d'analisi (COA)

Lot/Batch Number
122228502V
122228475V
122228237V
12222886V
122228-86V

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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
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
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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