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(+)-Abscisic acid

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(+)-Abscisic acid Basic information
Product Name:(+)-Abscisic acid
Synonyms:(ABA)ABSCISIC ACID >98%;(+)-Abscisic acid;ABA, Dormin, (S)-5-(1-Hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl)-3-methyl-(2Z,4E)-pentadienoic acid;S-(+)-ABA;[S]-5-[1-HYDROXY-2,6,6-TRIMETHYL-4-OXOCYCLOHEX-2-EN-1-YL]-3-METHYL-[2Z,4E]-PENTADIENOIC ACID;(+)-cis-abscisicacid;(s-(z,e))-methyl;abscisinii
CAS:21293-29-8
MF:C15H20O4
MW:264.32
EINECS:244-319-5
Product Categories:plantgrowth;Agro-Products;Sesqui-Terpenoids;Plant Hormones;Chiral Reagents;Biochemistry;Plant Growth Regulators;Plant Growth Trgulators (Others);Pharmaceutical Raw Materials;Inhibitors;Plant Growth regulator;21293-29-8
Mol File:21293-29-8.mol
(+)-Abscisic acid Structure
(+)-Abscisic acid Chemical Properties
Melting point 188 °C
alpha D20 +411.1° (c = 1 in ethanol); D20 +426.5° (c = 1 in 0.005N methanolic H2SO4)
Boiling point 327.55°C (rough estimate)
density 1.0583 (rough estimate)
refractive index 410 ° (C=0.2, EtOH)
storage temp. 2-8°C
solubility Chloroform (Slightly), Ethanol (Sparingly), Methanol (Slightly)
pka4.87±0.33(Predicted)
form Off-white powder
color White to Pale Yellow
Optical Rotation[α]/D 415±10°, c = 0.1 in ethanol
Merck 14,11
BRN 2698956
Stability:Light Sensitive
InChI1S/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
InChIKeyJLIDBLDQVAYHNE-WEYXYWBQSA-N
SMILESCC(\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C)=C\C(O)=O
LogP1.896 (est)
CAS DataBase Reference21293-29-8(CAS DataBase Reference)
EPA Substance Registry System2,4-Pentadienoic acid, 5-[(1S)-1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl]-3-methyl-, (2Z,4E)- (21293-29-8)
Safety Information
Safety Statements 22-24/25
WGK Germany 3
RTECS RZ2475100
8
HS Code 29189900
Storage Class11 - Combustible Solids
Hazard ClassificationsAquatic Acute 1
Aquatic Chronic 1
MSDS Information
ProviderLanguage
(+)-Abscisic acid English
SigmaAldrich English
(+)-Abscisic acid Usage And Synthesis
Chemical Properties(+)-Abscisic acid (pure substance) is a colorless crystalline solid. It has a melting point of 160–161°C and sublimes at 120°C. The partition coefficients are 1.8 for the electrically neutral form and 0.94 for the ionic form. Its relative density is 1.21. The solubility in water is 3102 mg/L (at pH 4). The specific rotation is [α]²⁰D = +40.997° (c = 10.1 mg/mL in ethanol, at 20°C). The pKa is 4.61. It is soluble in chloroform, acetone, ethyl acetate, and diethyl ether but only sparingly soluble in benzene and water. The UV maximum absorption wavelength (in methanol) is 252 nm.
Uses(+)-Abscisic acid is the natural isomer of the abscission-accelerating plant hormone and a plant growth regulator that exhibits multiple physiological effects, including inducing plant dormancy, inhibiting seed germination and plant growth, and stimulating stomatal closure.
DefinitionChEBI: The naturally occurring (1'S)-(+) enantiomer of abscisic acid. It is an important sesquiterpenoid plant hormone which acts as a regulator of plant responses to environmental stresses such as drought and cold.
Biochem/physiol ActionsPlant 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.
SynthesisEnantioselective total synthesis of (+)-Abscisic acid (ABA)[1]:
( )-Abscisic acid synthesis
storage-20°C
Purification MethodsCrystallise 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.]
References[1] Concise and Practical Total Synthesis of (+)-Abscisic Acid. ACS Omega 2020, 5, 22, 13296–13302. DOI:10.1021/acsomega.0c01332
(+)-Abscisic acid Preparation Products And Raw materials
Tag:(+)-Abscisic acid(21293-29-8) Related Product Information
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