ContaminantDB: Dikegulac

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 06:16:52 UTC

Update Date

2026-04-15 17:00:32 UTC

Accession Number

CHEM019556

Identification

Common Name

Dikegulac

Class

Small Molecule

Description

Diprogulic acid (also known as dikegulac) is a precursor used in commercial ascorbic acid production. In agriculture, its sodium salt, dikegulac sodium, is used as a plant growth regulator, primarily used as a branching agent. When it is taken up by a plant, dikegulac sodium is translocated to its apical meristems, where it inhibits DNA synthesis. This suppresses apical dominance in the plant and can stimulate lateral branching, resulting in a bushier growth habit. Dikegulac sodium is sometimes used to inhibit fruiting and flowering.

Contaminant Sources

ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Diprogulic acid	Kegg
Diprogulate	Generator
(3Ar,4as,8ar,8BS)-2,2,7,7-tetramethyl-4a,5,8a,8b-tetrahydro-[1,3]dioxolo[3,4]furo[1,3-D][1,3]dioxine-3a-carboxylate	Generator

Chemical Formula

C₁₂H₁₈O₇

Average Molecular Mass

274.269 g/mol

Monoisotopic Mass

274.105 g/mol

CAS Registry Number

18467-77-1

IUPAC Name

(1R,2S,6R,8S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[6.4.0.0²,⁶]dodecane-6-carboxylic acid

Traditional Name

(1R,2S,6R,8S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[6.4.0.0²,⁶]dodecane-6-carboxylic acid

SMILES

[H][C@]12COC(C)(C)O[C@@]1([H])[C@]1([H])OC(C)(C)O[C@@]1(O2)C(O)=O

InChI Identifier

InChI=1S/C12H18O7/c1-10(2)15-5-6-7(17-10)8-12(16-6,9(13)14)19-11(3,4)18-8/h6-8H,5H2,1-4H3,(H,13,14)/t6-,7+,8-,12+/m0/s1

InChI Key

FWCBATIDXGJRMF-FLNNQWSLSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Ketals

Alternative Parents

Substituents

Ketal
Monosaccharide
Meta-dioxane
Tetrahydrofuran
Meta-dioxolane
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

dioxanes (CHEBI:81986 )
Pesticides (C18825 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	8 g/L	ALOGPS
logP	0.86	ALOGPS
logP	1.12	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	3.05	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	83.45 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	60.72 m³·mol⁻¹	ChemAxon
Polarizability	26.48 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0190000000-0484a777050511a8d970	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05ot-1690000000-38cb26055d07239ae615	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9300000000-61cf1b2fde7189054572	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00fr-0290000000-abc6b99b64e3154a348d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-2190000000-ff29cc88f74439387a23	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9100000000-41d5d4fd99edf6008422	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Diprogulic acid

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

65420

Kegg Compound ID

C18825

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Dikegulac (CHEM019556)

Structure for CHEM019556: Dikegulac