(1R,2R,5S,8S,9S,10R,11S,12S)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.15,8.01,10.02,8]heptadec-13-ene-9-carboxylic acid

• ChemBase ID: 152750
• Molecular Formular: C19H22O6
• Molecular Mass: 346.37438
• Monoisotopic Mass: 346.14163842
• SMILES: C[C@@]12[C@H](C=C[C@@]3([C@H]1[C@@H]([C@]14[C@H]3CC[C@](C1)(C(=C)C4)O)C(=O)O)OC2=O)O
• Canonical SMILES: OC(=O)[C@H]1[C@@H]2[C@]3([C@H]4[C@]51CC(=C)[C@](C5)(O)CC4)C=C[C@@H]([C@@]2(C)C(=O)O3)O
• InChI: InChI=1S/C19H22O6/c1-9-7-17-8-18(9,24)5-3-10(17)19-6-4-11(20)16(2,15(23)25-19)13(19)12(17)14(21)22/h4,6,10-13,20,24H,1,3,5,7-8H2,2H3,(H,21,22)/t10-,11+,12-,13-,16-,17+,18+,19-/m1/s1
• InChIKey: IXORZMNAPKEEDV-OBDJNFEBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,5S,8S,9S,10R,11S,12S)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^5,^8.0^1,^1^0.0^2,^8]heptadec-13-ene-9-carboxylic acid
• IUPAC Traditional name: gibberellinsaeure
• Synonyms: Gibberellic acid; Gibberellin; U - 1,2-Dibromoethane solution; GA3; Gibberellin A3; Gibberellic acid; 二溴化乙烯; 1,2-二溴乙烷 溶液; 赤霉素 A3; 赤霉酸

Database IDs

• CAS Number: 106-93-4; 77-06-5
• EC Number: 201-001-0
• MDL Number: MFCD00079329
• Beilstein Number: 54346
• PubChem SID: 24872426; 24882703; 24872417; 24899234; 162246893; 24862569
• PubChem CID: 6466

CALCULATED PROPERTIES

• Acid pKa: 4.163467
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.0024102
• LogD (pH = 7.4): -2.7070677
• Log P: 0.3509133
• Molar Refractivity: 86.4155 cm^3
• Polarizability: 34.211063 Å^3
• Polar Surface Area: 104.06 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]20/D +78±5°, c = 2% in methanol; [α]20/D +80±3°, c = 1% in methanol; [α]20/D +83±3°, c = 2.1% in ethanol

Safety Information

• RTECS: LY8990000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2; 3
• Risk Statements: 36
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥95% (HPLC); 80% gibberellin A3 basis (TLC); 90% gibberellin A3 basis (HPLC)
• Grade: analytical standard; PESTANAL®, analytical standard
• Packaging: ampule of 100 mg
• Empirical Formula (Hill Notation): C19H22O6

DETAILS

Sigma Aldrich - 48870

Biochem/physiol Actions
A "classical" ubiquitous plant hormone, with diverse effects, such as stilumating stem and root growth, and stimulating seed germination.1
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 48870.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 48880

General description
Gibberellic acid is an endogenous plant growth regulator
Other Notes
Structure-activity studies2
Biochem/physiol Actions
Phytohormone that controls important aspects of plant growth: germination, elongation, and flowering. The effects are mediated by inducing degradation of the DELLA repressor protein, and probably other minor signalling pathways.1

Sigma Aldrich - 63492

General description
Gibberellic acid is an endogenous plant growth regulator
Biochem/physiol Actions
Phytohormone that controls important aspects of plant growth: germination, elongation, and flowering. The effects are mediated by inducing degradation of the DELLA repressor protein, and probably other minor signalling pathways.1

Sigma Aldrich - 36575

General description
Gibberellic acid is an endogenous plant growth regulator
Biochem/physiol Actions
Phytohormone that controls important aspects of plant growth: germination, elongation, and flowering. The effects are mediated by inducing degradation of the DELLA repressor protein, and probably other minor signalling pathways.1
Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

Sigma Aldrich - 48880

General description
Gibberellic acid is an endogenous plant growth regulator
Other Notes
Structure-activity studies2
Biochem/physiol Actions
Phytohormone that controls important aspects of plant growth: germination, elongation, and flowering. The effects are mediated by inducing degradation of the DELLA repressor protein, and probably other minor signalling pathways.1

Sigma Aldrich - PS49

General description
Gibberellic acid is an endogenous plant growth regulator
Biochem/physiol Actions
Phytohormone that controls important aspects of plant growth: germination, elongation, and flowering. The effects are mediated by inducing degradation of the DELLA repressor protein, and probably other minor signalling pathways.1