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Gibbane-1,10-dicarboxylic acid, 2,3-epoxy-4a,7-dihydroxy-1-methyl-8-methylene-, 1,4a-lactone, (1alpha,2beta,3beta,4aalpha,4bbeta,10beta)-

HCID 443449
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Basic information

CAS
19147-78-5
Standard SMILES
C=C1C[C@]23C[C@@]1(O)CC[C@H]2[C@@]12C[C@@H]4O[C@@H]4C(C)(C(=O)O1)[C@H]2[C@@H]3C(=O)O
InChIKey
XNBWKKYPKJHUKD-JXHFLFEZSA-N
Molecular formula
C19H22O6
Average molar mass
346.4 g/mol
Monoisotopic mass
346.14163842

Names & identifiers

Preferred name
Gibbane-1,10-dicarboxylic acid, 2,3-epoxy-4a,7-dihydroxy-1-methyl-8-methylene-, 1,4a-lactone, (1alpha,2beta,3beta,4aalpha,4bbeta,10beta)-
IUPAC
(1R,2R,5S,8S,9S,10R,12R,14S)-5-hydroxy-11-methyl-6-methylidene-17-oxo-13,16-dioxahexacyclo[9.4.2.15,8.01,10.02,8.012,14]octadecane-9-carboxylic acid
English name
2β,3β-Epoxy-4aα,7-dihydroxy-1β-methyl-8-methylenegibbane-1α,10β-dicarboxylic acid 1,4a-lactone
Molecular formula
C19H22O6
Molecular weight
346.38

Names & synonyms

Gibbane-1,10-dicarboxylic acid, 2,3-epoxy-4a,7-dihydroxy-1-methyl-8-methylene-, 1,4a-lactone, (1alpha,2beta,3beta,4aalpha,4bbeta,10beta)-SCHEMBL30194786GA6Gibberellin A6ent-2α,3α-epoxy-13-hydroxy-20-norgibberell-16-en-19-oic acid 19,10-lactone2β,3β-Epoxy-4aα,7-dihydroxy-1β-methyl-8-methylenegibbane-1α,10β-dicarboxylic acid 1,4a-lactoneGibbane-1,10-dicarboxylic acid, 2,3-epoxy-4a,7-dihydroxy-1-methyl-8-methylene-, 1,4a-lactone, (1α,2β,3β,4aα,4bβ,10β)-(1aS,2aR,2bR,5S,7aS,8S,8aR,9S,9aR)-5-hydroxy-9-methyl-6-methylene-10-oxododecahydro-2a,9-(epoxymethano)-5,7a-methanocyclohepta[1,2]indeno[5,6-b]oxirene-8-carboxylic acid

Database identifiers

CAS
19147-78-5
PubChem CID
443449

Properties

Computed structural properties

XLogP
0.2
Topological polar surface area
96.4 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
6
Rotatable bonds
1
Heavy atoms
25
Formal charge
0
Complexity
776

Physicochemical properties

Melting point
206 °C · >206°C (dec.)
Boiling point
609.9 · 609.9±55.0 °C(Predicted)
Density
1.51 · 1.51±0.1 g/cm3(Predicted)
storage temp.
-20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
solubility
Chloroform (Slightly), Methanol (Slightly)
form
Solid
pka
4.16 · 4.16±0.60(Predicted)
color
White to Off-White
Stability
Moisture Sensitive
EPA Substance Registry System
6 · Gibberellin A6 (19147-78-5)

Chemistry & industry

Applications

UsesGibberellin A6 is a derivative of the plant hormone Gibberellin which regulates growth and various developmental processes.

Additional notes · 1 item

DefinitionChEBI: Gibberellin A6 is a C19-gibberellin, initially identified in Phaseolus coccineus and differing from gibberellin A1 by the conversion of the OH at C-2 (gibbane numbering) into an epoxide across C-2 and C-3. It is a lactone, a C19-gibberellin and a gibberellin monocarboxylic acid.

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