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77-06-5 molecular structure
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(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 and InChIs

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

Cite this record

CBID:152750 http://www.chembase.cn/molecule-152750.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(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
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
CAS Number
77-06-5
106-93-4
EC Number
201-001-0
MDL Number
MFCD00079329
Beilstein Number
54346
PubChem SID
24872417
24872426
24882703
162246893
24862569
24899234
PubChem CID
6466

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 6466 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 4.163467  H Acceptors
H Donor LogD (pH = 5.5) -1.0024102 
LogD (pH = 7.4) -2.7070677  Log P 0.3509133 
Molar Refractivity 86.4155 cm3 Polarizability 34.211063 Å3
Polar Surface Area 104.06 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Optical Rotation
[α]20/D +78±5°, c = 2% in methanol expand Show data source
[α]20/D +80±3°, c = 1% in methanol expand Show data source
[α]20/D +83±3°, c = 2.1% in ethanol expand Show data source
RTECS
LY8990000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
3 expand Show data source
Risk Statements
36 expand Show data source
Safety Statements
26-36 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H319 expand Show data source
GHS Precautionary statements
P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Purity
≥95% (HPLC) expand Show data source
80% gibberellin A3 basis (TLC) expand Show data source
90% gibberellin A3 basis (HPLC) expand Show data source
Grade
analytical standard expand Show data source
PESTANAL®, analytical standard expand Show data source
Packaging
ampule of 100 mg expand Show data source
Empirical Formula (Hill Notation)
C19H22O6 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - 48870 external link
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 external link
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 external link
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 external link
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 - PS49 external link
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 - 48880 external link
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

REFERENCES

REFERENCES

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PATENTS

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