(1R,2R,5S,8R,9S,10R,11S,12S)-12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.15,8.01,10.02,8]heptadecane-9-carboxylic acid

• ChemBase ID: 133194
• Molecular Formular: C19H24O5
• Molecular Mass: 332.39086
• Monoisotopic Mass: 332.16237387
• SMILES: C[C@@]12[C@H](CC[C@@]3([C@@H]1[C@@H]([C@]14[C@H]3CC[C@H](C1)C(=C)C4)C(=O)O)OC2=O)O
• Canonical SMILES: C=C1C[C@@]23C[C@H]1CC[C@H]3[C@@]13[C@H]([C@@H]2C(=O)O)[C@@](C)([C@H](CC1)O)C(=O)O3
• InChI: InChI=1S/C19H24O5/c1-9-7-18-8-10(9)3-4-11(18)19-6-5-12(20)17(2,16(23)24-19)14(19)13(18)15(21)22/h10-14,20H,1,3-8H2,2H3,(H,21,22)/t10-,11+,12-,13+,14+,17+,18-,19+/m0/s1
• InChIKey: RSQSQJNRHICNNH-OZGZIUBOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,5S,8R,9S,10R,11S,12S)-12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^5,^8.0^1,^1^0.0^2,^8]heptadecane-9-carboxylic acid
• IUPAC Traditional name: (1R,2R,5S,8R,9S,10R,11S,12S)-12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^5,^8.0^1,^1^0.0^2,^8]heptadecane-9-carboxylic acid
• Synonyms: Gibberellin A4

Database IDs

• CAS Number: 468-44-0
• EC Number: 207-406-9
• MDL Number: MFCD00133363
• PubChem SID: 162227471; 24895150
• PubChem CID: 3034393

CALCULATED PROPERTIES

• Acid pKa: 4.288334
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.32484943
• LogD (pH = 7.4): -1.4111365
• Log P: 1.5603198
• Molar Refractivity: 84.0788 cm^3
• Polarizability: 33.795246 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥90%
• Suitability: plant cell culture tested
• Impurities: ≤5% gibberellin A7

DETAILS

Sigma Aldrich - G7276

Application
Gibberillic acids (GA) are important plant growth hormones that promote plant cell growth and elongation. Gebberillins promote rapid stem and root growth, induce mitotic division and initiate (break dormancy) and increase seed germination rates. The gibberellins are also involved in processes such as gravitropism, tensioning and floral display.Gibberellin A3 (G1025, G7645) and A4 (G7276) may be used as supplements to plant growth media such as Murashige and Skoog media. The specific actions of A3 and A4 or combinations of Gebberellins should be determined in specific plant applications.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. G7276.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.