(2Z,4E)-5-[(1S)-1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid

• ChemBase ID: 125576
• Molecular Formular: C15H20O4
• Molecular Mass: 264.3169
• Monoisotopic Mass: 264.13615912
• SMILES: OC(=O)/C=C(/C)\C=C\[C@@]1(O)C(=CC(=O)CC1(C)C)C
• Canonical SMILES: OC(=O)/C=C(\C=C\[C@@]1(O)C(=CC(=O)CC1(C)C)C)/C
• InChI: 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-YKALOCIXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z,4E)-5-[(1S)-1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid
• IUPAC Systematic name: (2Z,4E)-5-[(1S)-1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid
• IUPAC Traditional name: abscisic acid
• Synonyms: (2Z,4E)-(S)-5-(1-Hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl)-3-methyl-2,4-pentanedienoic acid; Abscisic acid; Dormin; Abscisic acid; (S-(Z,E)])-5-(1-Hydroxy-2,6,6-trimethyl)-4-oxo-2-cyclohexen-1-yl-3-methyl-2,4-pentadienoic Acid; (+)-(S)-Abscisic Acid; (+)-(cis,trans)-Abscisic Acid; (+)-ABA; S-ABA; (+)-cis,trans-Abscisic Acid, 98%; (S)-5-(1-Hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl)-3-methyl-(2Z,4E)-pentadienoic acid; ABA; (+)-Abscisic acid; 休眠素

Database IDs

• CAS Number: 21293-29-8
• EC Number: 244-319-5
• MDL Number: MFCD00066545
• Beilstein Number: 2698956
• PubChem SID: 24890921; 24844958; 162219926
• PubChem CID: 5280896
• CHEBI ID: 2635
• CHEMBL: 288040
• Chemspider ID: 4444418
• MeSH Name: Abscisic+Acid
• Wikipedia Title: Abscisic_acid

CALCULATED PROPERTIES

• Acid pKa: 4.7381496
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.2628527
• LogD (pH = 7.4): -0.5142804
• Log P: 2.0932755
• Molar Refractivity: 74.9764 cm^3
• Polarizability: 28.11777 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Colorless crystals; Powder; White Powder
• Melting Point: 161-163C; 163°C
• Boiling Point: 458.7°C (sublimes)
• Density: 1.193 g/mL
• Partition Coefficient: 1.896
• pKa: 4.868
• pKb: 9.129

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: RZ2475100
• German water hazard class: 3
• Safety Statements: S22, S24/25
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥98% (HPLC); 99% (CH)
• Grade: puriss.
• Empirical Formula (Hill Notation): C15H20O4

DETAILS

Sigma Aldrich - A4906

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
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.
Other Notes
Natural isomer of the abscission-accelerating plant hormone.
Application
(+)-Abscisic acid is a plant hormone and growth regulator involved in several physiological mechanisms including seed dormancy, leaf abscission, stomatal movement, and plant stress responses such as drought. Abscisic acid has been used in a study to learn about expression analysis of four peroxiredoxin genes from Tamarix hispida.

Sigma Aldrich - 00012

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.
Other Notes
Natural plant growth regulator1; High-affinity binding sites for abscisic acid on the plasmalemma of Vicia faba guard cells2

Toronto Research Chemicals - A110000

The natural isomer of the abscission-accelerating plant hormone.

REFERENCES

• Krochko, J.E., et al.: Plant Physiol., 118, 849 (1998)
• Jacobsen, J.V., et al.: Psysiol. Plant., 115, 428 (1998)