SMB00089

Dehydroabietic acid

≥90% (LC/MS-ELSD)

• Synonym(e): Abieta-8,11,13-trien-18-oic acid, Dehydroabietate
• Empirische Formel (Hill-System): C₂₀H₂₈O₂
• CAS-Nummer: 1740-19-8
• Molekulargewicht: 300.44
• EG-Nummer: 217-102-8
• MDL-Nummer: MFCD09839012
• UNSPSC-Code: 12352205
• PubChem Substanz-ID: 329824767
• NACRES: NA.25

Eigenschaften

• Assay: ≥90% (LC/MS-ELSD)
• Form: solid
• Anwendung(en): metabolomics; vitamins, nutraceuticals, and natural products
• Lagertemp.: −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
• InChIKey: NFWKVWVWBFBAOV-MISYRCLQSA-N

Beschreibung

Allgemeine Beschreibung

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]

Anwendung

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]

Biochem./physiol. Wirkung

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]

Sicherheitshinweise

• Piktogramme: GHS06,GHS09
• Signalwort: Danger
• H-Sätze: H301,H410
• P-Sätze: P273 - P301 + P310 + P330
• Gefahreneinstufungen: Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1
• Lagerklassenschlüssel: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 1
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable