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
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About This Item
Empirical Formula (Hill Notation):
C15H20O4
CAS Number:
Molecular Weight:
264.32
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Quality Level
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
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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).
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
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Scott Hayes et al.
Current biology : CB, 29(10), 1669-1676 (2019-05-06)
Global food production is set to keep increasing despite a predicted decrease in total arable land [1]. To achieve higher production, denser planting will be required on increasingly degraded soils. When grown in dense stands, crops elongate and raise their
Mirko Magnone et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 29(12), 4783-4793 (2015-08-06)
2-Cis,4-trans-abscisic acid (ABA) is a plant hormone that is present also in animals. Several lines of evidence suggest that ABA contributes to the regulation of glycemia in mammals: nanomolar ABA stimulates insulin release from β-pancreatic cells and glucose transporter-4-mediated glucose
Haifeng Jia et al.
The New phytologist, 198(2), 453-465 (2013-02-22)
Fleshy fruits are classically divided into climacteric and nonclimacteric types. It has long been thought that the ripening of climacteric and nonclimacteric fruits is regulated by ethylene and abscisic acid (ABA), respectively. Here, we report that sucrose functions as a
Kamil Frankowski et al.
Postepy biochemii, 59(1), 83-88 (2013-07-05)
Abscisic acid is one of the plant hormones that determines normal growth and development, i.e. seeds ripening and germination, stomata opening and closure, flowering and stress responses. An appropriate level of endogenous ABA plays a key role in the regulation
Alexandra Pokhilko et al.
BMC systems biology, 7, 23-23 (2013-03-20)
24-hour biological clocks are intimately connected to the cellular signalling network, which complicates the analysis of clock mechanisms. The transcriptional regulator TOC1 (TIMING OF CAB EXPRESSION 1) is a founding component of the gene circuit in the plant circadian clock.
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