A DAF-12 ligand that controls C. elegans development and lifespan
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Isomer(s)
14100Δ4-Dafachronic Acid
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(25S)-Δ7-Dafachronic Acid

Item No. 14101

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5α,25S)-3-oxo-cholest-7-en-26-oic acid
CAS Number
949004-12-0
Synonyms
  • (25S)-Δ7-DA
  • UPF-1404
Molecular Formula
C27H42O3
Formula Weight
414.6
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 5 mg/mlDMSO: 2.5 mg/mlEthanol: 12.5 mg/mlEthanol:PBS (pH 7.2) (1:10): 0.1 mg/ml
SMILES
O=C1CC[C@@]2(C)[C@](CC=C3[C@]2([H])CC[C@@]4(C)[C@@]3([H])CC[C@@H]4[C@@H](CCC[C@H](C)C(O)=O)C)([H])C1
InChi Code
InChI=1S/C27H42O3/c1-17(6-5-7-18(2)25(29)30)22-10-11-23-21-9-8-19-16-20(28)12-14-26(19,3)24(21)13-15-27(22,23)4/h9,17-19,22-24H,5-8,10-16H2,1-4H3,(H,29,30)/t17-,18+,19+,22-,23+,24+,26+,27-/m1/s1
InChi Key
SQTAVUCHOVVOFD-OBRBSRNPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 µg

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    Product Description

    (25S)-Δ7-Dafachronic acid is a sterol-derived hormone that acts as a ligand of DAF-12 with an EC50 value of 23 nM.1,2,3,4 At 50 nM, (25S)-Δ7-Dafachronic acid inhibits the dauer-promoting activity of DAF-12, blocking the formation of infective larvae in several parasitic nematodes in favor of reproductive maturation to adults.5,6 Thus, selective ligand modulators of DAF-12 are a potential therapeutic approach to stop larvae progression during parasitic infection.7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Martin, R., Däbritz, F., Entchev, E.V., et al. Stereoselective synthesis of the hormonally active (25S)-Δ7-dafachronic acid, (25S)-Δ4-dafachronic acid, (25S)-dafachronic acid, and (25S)-cholestenoic acid. Org. Biomol. Chem. 6(23), 4293-4295 (2008).

    2. Motola, D.L., Cummins, C.L., Rottiers, V., et al. Identification of ligands for DAF-12 that govern dauer formation and reproduction in C. elegans. Cell 124(6), 1209-1223 (2006).

    3. Sharma, K.K., Wang, Z., Motola, D.L., et al. Synthesis and activity of dafachronic acid ligands for the C. elegans DAF-12 nuclear hormone receptor. Mol. Endocrinol. 23(5), 640-648 (2009).

    4. Beckstead, R.B., and Thummel, C.S. Indicted: Worms caught using steroids. Cell 124(6), 1137-1140 (2006).

    5. Martin, R., Entchev, E.V., Kurzchalia, T.V., et al. Steroid hormones controlling the life cycle of the nematode Caenorhabditis elegans: Stereoselective synthesis and biology. Org. Biomol. Chem. 8(4), 739-750 (2010).

    6. Ogawa, A., Streit, A., Antebi, A., et al. A conserved endocrine mechanism controls the formation of dauer and infective larvae in nematodes. Curr. Biol. 19(1), 67-71 (2009).

    7. Wang, Z., Zhou, X.E., Motola, D.L., et al. Identification of the nuclear receptor DAF-12 as a therapeutic target in parasitic nematodes. Proc. Natl. Acad. Sci. USA 106(23), 9138-9143 (2009).