862169

2-cis,4-trans-Abscisic acid

synthetic, 98%

• Synonym(s): (±)-Abscisic acid, (2Z,4E)-5-(1-Hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl)-3-methyl-2,4-pentadienoic acid, ABA, Dormin
• Empirical Formula (Hill Notation): C₁₅H₂₀O₄
• CAS Number: 14375-45-2
• Molecular Weight: 264.32
• MDL number: MFCD00075619
• UNSPSC Code: 12352100
• PubChem Substance ID: 24888569
• NACRES: NA.22

Properties

• Quality Level: 100
• Assay: 98%
• form: powder
• mp: 186-188 °C (lit.)
• functional group: carboxylic acid; hydroxyl; ketone
• storage temp.: 2-8°C
• SMILES string: CC(\C=C\C1(O)C(C)=CC(=O)CC1(C)C)=C\C(O)=O
• InChI: 1S/C15H20O4/c1-10(7-13(17)18)5-6-15(19)11(2)8-12(16)9-14(15,3)4/h5-8,19H,9H2,1-4H3,(H,17,18)/b6-5+,10-7-
• InChI key: JLIDBLDQVAYHNE-LXGGSRJLSA-N

Description

General description

2-cis,4-trans-Abscisic acid (ABA) is an organic compound used as a starting material in in organic synthesis. It is also used as a chiral auxiliary during asymmetric synthesis. ABA derivatives can be used to control the stereochemistry of reactions by serving as chiral templates that induce the formation of specific products.

Application

• Chiral Separation of Abscisic Acid: Research demonstrated direct chiral separation of abscisic acid using high-performance liquid chromatography with a phenyl column and a gamma-cyclodextrin mobile phase, advancing the analytical methods essential for studying plant stress hormones (Terashima et al., 2023).


• Xanthine Oxidase Inhibitory Activity: A study including abscisic acid derivatives showed significant xanthine oxidase inhibitory activity, offering potential health benefits and therapeutic applications (Miyata et al., 2019).


• Anticancer Potential: Extracts containing abscisic acid from mangrove endophytic fungi exhibited cytotoxic properties and induced G(0)/G(1) cell cycle arrest and apoptosis in human cancer cells, highlighting their potential in cancer treatment strategies (Zhou et al., 2018).


• Antidiabetic Activity: Extracts involving abscisic acid from an endophytic fungus showed promising antidiabetic activity, potentially improving treatment options for diabetes through natural product research (Uzor et al., 2017).


• Glucose Tolerance and Insulinemia Reduction: A groundbreaking study found that microgram amounts of abscisic acid in fruit extracts significantly improve glucose tolerance and reduce insulin levels in rats and humans, suggesting its use as a dietary supplement for managing diabetes (Magnone et al., 2015).

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves