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862169

Sigma-Aldrich

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:
14375-45-2
Molecular Weight:
264.32
MDL number:
MFCD00075619
UNSPSC Code:
12352100
PubChem Substance ID:
24888569
NACRES:
NA.22
Pricing and availability is not currently available.

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

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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. [1]

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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Certificates of Analysis (COA)

Lot/Batch Number
MKCW0718
WXBF4434V
MKCS8570
MKCR8841
MKCR5499

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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
Scott A M McAdam et al.
The New phytologist, 198(2), 429-441 (2013-02-21)
Little is known about how a predominantly passive hydraulic stomatal control in ferns and lycophytes might impact water use under stress. Ferns and lycophytes occupy a diverse array of habitats, from deserts to rainforest canopies, raising the question of whether
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
Helene Persak et al.
PloS one, 8(2), e57547-e57547 (2013-02-26)
Abiotic stress poses a huge, ever-increasing problem to plants and agriculture. The dissection of signalling pathways mediating stress tolerance is a prerequisite to develop more resistant plant species. Mitogen-activated protein kinase (MAPK) cascades are universal signalling modules. In Arabidopsis, the
View All Related Papers

Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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