| Identification | Back Directory | [Name]
Δ4-Dafachronic acid | [CAS]
23017-97-2 | [Synonyms]
Δ4-Dafachronic acid
.delta.4-Dafachronic Acid
PSXQJZDFWDKBIP-NNWQCNCGSA-N
3-Oxocholest-4-en-26-oic acid
Δ4-Dafachronic Acid Exclusive
Cholest-4-en-26-oic acid, 3-oxo- | [Molecular Formula]
C27H42O3 | [MOL File]
23017-97-2.mol | [Molecular Weight]
414.62 |
| Chemical Properties | Back Directory | [Boiling point ]
554.6±19.0 °C(Predicted) | [density ]
1.07±0.1 g/cm3(Predicted) | [solubility ]
DMF: 5 mg/ml; DMSO: 2.5 mg/ml; Ethanol: 12.5 mg/ml; Ethanol:PBS (pH 7.2) (1:10): 0.09 mg/ml | [form ]
A crystalline solid | [pka]
4.81±0.21(Predicted) | [color ]
White to off-white |
| Hazard Information | Back Directory | [Description]
During unfavorable environmental conditions, C. elegans larvae undergo arrest and form dauer larvae that can attach to other animals as a parasitic strategy for survival. DAF-12 is an orphan nuclear hormone receptor that regulates dauer larva diapause, reproductive development, fat metabolism, and life cycle/longevity in C. elegans. DAF-12 is required for entry into dauer when it is not bound to ligand by acting as a transcriptional repressor of target genes that favor reproductive development. Δ4-Dafachronic acid is a racemic version of a sterol-derived hormone that acts as a ligand of DAF-12. Δ4-Dafachronic acid binds to and transactivates DAF-12, rescuing hormone deficiency in transgenic dauer larvae and promoting reproductive maturation into adults. The (25S) diastereomer of Δ4-dafachronic acid is significantly more potent than its (25R) counterpart (EC50s = 23 and 66 nM, respectively). | [Uses]
Δ4-Dafachronic acid is an agonist of DAF-12 and a metabolite of cholesterol[1]. | [Definition]
ChEBI: Delta(4)-dafachronic acid is a cholestanoid that is cholest-4-en-26-oic acid which is substituted at position 3 by an oxo group. It is a 3-oxo-Delta(4) steroid, a member of dafachronic acids and a C27-steroid. It is a conjugate acid of a Delta(4)-dafachronate. | [References]
[1] Amie L T Romney, et al. Temperature-dependent vitamin D signaling regulates developmental trajectory associated with diapause in an annual killifish. Proc Natl Acad Sci U S A. 2018 Dec 11;115(50):12763-12768. DOI:10.1073/pnas.1804590115 |
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