21293-29-8 Usage
Description
(+)-Abscisic acid, also known as abscisic acid, is the naturally occurring (1'S)-(+) enantiomer of abscisic acid. It is an important sesquiterpenoid plant hormone that plays a crucial role in regulating plant responses to environmental stresses such as drought and cold. It is a white powder in its chemical form.
Uses
Used in Pharmaceutical Industry:
(+)-Abscisic acid is used as a pharmaceutical intermediate for the synthesis of Valacyclovir, an antiviral medication used to treat various viral infections, including herpes simplex and varicella-zoster virus.
Used in Agriculture:
(+)-Abscisic acid is used as a plant growth regulator to enhance the stress tolerance and improve the overall growth and productivity of crops. It helps plants to adapt to environmental stresses such as drought and cold, ensuring better crop yields and quality.
Used in Plant Biotechnology:
(+)-Abscisic acid is used in plant biotechnology research to study the molecular mechanisms of plant stress responses and develop genetically modified plants with improved stress tolerance and resilience. This can contribute to the development of more sustainable and climate-resilient agricultural practices.
Biochem/physiol Actions
Plant hormone and growth regulator that is involved in several physiological mechanisms including seed dormancy, leaf abscission, stomatal movement, and plant stress responses. Through complex interactions with several intracellular signaling systems, it can regulate the expression of hundreds of plant genes.
Purification Methods
Crystallise the acid from CCl4/pet ether, EtOH/hexane and sublime it at 120o. Also purify it by dissolving ~30g in 30mL of EtOAc, adding 100mL of hexane and allow to crystallise overnight (yield 8.4g), m 156-158o, 161-163o, [] D +426o (c 0.005M H2SO4 in MeOH). [Cornforth et al. Nature (London) 206 715 1965, Soukemp et al. Helv Chim Acta 72 361 1989.] The RS-isomer was purified on a Kieselgel F254 plate with toluene/EtOAc/AcOH (50:50:3) and has m 188-190o [Cornforth et al. Aust J Chem 45 179 1992]. [Beilstein 17/3 V 13.]
Check Digit Verification of cas no
The CAS Registry Mumber 21293-29-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,1,2,9 and 3 respectively; the second part has 2 digits, 2 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 21293-29:
(7*2)+(6*1)+(5*2)+(4*9)+(3*3)+(2*2)+(1*9)=88
88 % 10 = 8
So 21293-29-8 is a valid CAS Registry Number.
InChI:InChI=1/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-/t15-/m1/s1
21293-29-8Relevant articles and documents
A novel synthesis of (±)-abscisic acid
Gomes Constantino,Losco,Castellano
, p. 681 - 683 (1989)
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Synthesis and biological activity of abscisic acid esters
Wan, Chuan,Zhang, Yuanzhi,Yang, Dongyan,Han, Xiaoqiang,Li, Xiuyun,Li, Hong,Xiao, Yumei,Qin, Zhaohai
, p. 267 - 272 (2015/06/22)
Abstract 16 ABA esters including 11 new compounds were prepared by two different esterification routes. All the structures of ABA esters were confirmed by 1H NMR, 13C NMR and HRMS. Their biological activity and hydrolysis stability were investigated. Fortunately, there were 15 and 9 compounds which displayed much better or nearly the same inhibition activity for rice seedling growth and Arabidopsis thaliana seed germination compared to ABA, respectively. Especially, compounds 2d and 2g showed better biological activities than ABA in the three tests. Moreover, we found that chemical hydrolysis ability of the esters in vitro had little relationship to their biological activity.
Resolution of (+)-abscisic acid using an Arabidopsis glycosyltransferase
Lim, Eng-Kiat,Doucet, Charlotte J.,Hou, Bingkai,Jackson, Rosamond G.,Abrams, Suzanne R.,Bowles, Dianna J.
, p. 143 - 147 (2007/10/03)
Abscisic acid (ABA) can exist as two enantiomers, with (+)-ABA as the naturally occurring form. Typically, both enantiomers occur in chemical preparations and both can be modified in the plant to their respective glucose esters. To identify glycosyltransferases capable of discriminating between the different forms of ABA, the Family 1 enzymes of Arabidopsis thaliana were screened for activity towards (±)-ABA. Eight enzymes were found to recognise the plant hormone, with one UGT71B6 showing enantioselective glucosylation towards (+)-ABA. UGT71B6 was used in a whole-cell biocatalysis system as a means of separating (+)- and (-)-ABA, thereby offering an alternative to chemical synthesis for the production of pure (+)-ABA.