| Identification | More | [Name]
(+)-Abscisic acid | [CAS]
21293-29-8 | [Synonyms]
(2-CIS,4-TRANS, 1S)-5-(1-HYDROXY-2,6,6-TRIMETHYL-4-OXO-2-CYCLOHEXEN-1-YL)-3-METHYL-2,4-PENTADIENOIC ACID
ABA
ABK
(+)-ABSCISIC ACID
ABSCISIC ACID
ABSCISIC ACID, (+)-
ABSCISIN
(+)-CIS,TRANS-ABSCISIC ACID
DORMIN
[S]-5-[1-HYDROXY-2,6,6-TRIMETHYL-4-OXOCYCLOHEX-2-EN-1-YL]-3-METHYL-[2Z,4E]-PENTADIENOIC ACID
S-(+)-ABA
S-ABA
(S)-(+)-ABSCISIC ACID
(+)-abscisinii
(+)-cis-abscisicacid
(s-(z,e))-methyl
abscisinii
acideabscisique
cis-abscisicacid
dormin(abscissionfactor) | [EINECS(EC#)]
244-319-5 | [Molecular Formula]
C15H20O4 | [MDL Number]
MFCD00066545 | [Molecular Weight]
264.32 | [MOL File]
21293-29-8.mol |
| Chemical Properties | Back Directory | [Appearance]
White Powder | [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. ]
−20°C
| [solubility ]
Chloroform (Slightly), Ethanol (Sparingly), Methanol (Slightly) | [form ]
Off-white powder | [pka]
4.87±0.33(Predicted) | [color ]
White to Pale Yellow | [Optical Rotation]
[α]/D 415±10°, c = 0.1 in ethanol | [Usage]
The natural isomer of the abscission-accelerating plant hormone | [Merck ]
11 | [BRN ]
2698956 | [Stability:]
Light Sensitive | [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-/t15-/m1/s1 | [InChIKey]
JLIDBLDQVAYHNE-WEYXYWBQSA-N | [SMILES]
CC(\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C)=C\C(O)=O | [LogP]
1.896 (est) | [CAS DataBase Reference]
21293-29-8(CAS DataBase Reference) | [EPA Substance Registry System]
2,4-Pentadienoic acid, 5-[(1S)-1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl]-3-methyl-, (2Z,4E)- (21293-29-8) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P271-P280 | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [RTECS ]
RZ2475100
| [F ]
8 | [REACH Registrations]
Active | [HS Code ]
29189900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Aquatic Acute 1
Aquatic Chronic 1 |
| Hazard Information | Back Directory | [Chemical Properties]
White Powder | [Uses]
The natural isomer of the abscission-accelerating plant hormone | [Uses]
Valacyclovir intermediate | [Definition]
ChEBI: 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 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. | [Synthesis]
Enantioselective total synthesis of (+)-Abscisic acid (ABA)[1]:
 | [storage]
Store at -20°C | [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.] | [References]
[1] Concise and Practical Total Synthesis of (+)-Abscisic Acid. ACS Omega 2020, 5, 22, 13296–13302. DOI:10.1021/acsomega.0c01332
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Energy Chemical
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