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Ascr#5

Cat No.:V33952 Purity: ≥98%
Ascr#5 is a highly conserved ascaroside in Caenorhabditis elegans.
Ascr#5
Ascr#5 Chemical Structure CAS No.: 1086696-26-5
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
5mg
10mg
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Product Description
Ascr#5 is a highly conserved ascaroside in Caenorhabditis elegans.
Ascr#5 (CAS 1086696-26-5), also known as Ascaroside C3 or asc-omegaC3, is a highly conserved ascaroside pheromone found in Caenorhabditis elegans. It is an omega-hydroxy fatty acid ascaroside obtained by condensation of 3-hydroxypropanoic acid with ascarylopyranose. This compound plays key roles in dauer formation, lifespan regulation, aggregation, mating, and stress responses.
Biological Activity I Assay Protocols (From Reference)
Targets
Ascr#5 targets the nematode chemosensory system and the dauer formation signaling pathways. It functions as a pheromone-like cue that modulates a variety of responses in C. elegans and related species. The compound interacts with specific G protein-coupled receptors in the nematode sensory neurons, triggering downstream signaling cascades that regulate development and behavior.
ln Vitro
In vitro, Ascr#5 modulates developmental and behavioral responses in C. elegans in a concentration-dependent manner. It induces dauer formation at specific concentrations and influences aggregation and mating behaviors in liquid and solid media assays. The compound is typically tested using synchronized nematode populations to assess its effects on larval development, chemotaxis, and social behaviors.
ln Vivo
In vivo, Ascr#5 is a naturally occurring pheromone that regulates population density-dependent developmental decisions in C. elegans. At elevated concentrations, it promotes the formation of dauer larvae, a specialized stress-resistant stage, while at lower concentrations, it influences adult behaviors including aggregation and mating. The compound's effects are mediated through the insulin/IGF-1 and TGF-beta signaling pathways.
Enzyme Assay
In vitro receptor binding assays for Ascr#5 are performed using chemosensory neurons isolated from C. elegans or using heterologous expression systems expressing candidate ascaroside receptors. Radiolabeled or fluorescently labeled Ascr#5 is incubated with neuronal preparations or receptor-expressing cells, and binding affinity is measured. Calcium imaging is used to assess receptor activation in response to Ascr#5 stimulation.
Cell Assay
Cellular assays for Ascr#5 are conducted using C. elegans whole-organism platforms rather than traditional cell culture. Synchronized L1 larvae or adult worms are exposed to varying concentrations of Ascr#5 (1 nM to 100 uM) in liquid or agar plate assays. Endpoints include dauer formation rate, aggregation index, chemotaxis index, and lifespan measurement.
Animal Protocol
In vivo animal experiments for Ascr#5 utilize C. elegans as the model organism. Standard protocols involve preparing agar plates containing defined concentrations of Ascr#5. Synchronized worm populations are transferred to the plates and incubated at 25degC for dauer formation assays (48-72 hours) or at 20degC for behavioral assays (1-4 hours). Dauer larvae are identified by morphology and resistance to SDS treatment.
ADME/Pharmacokinetics
Pharmacokinetic data for Ascr#5 are not applicable, as the compound is used as a research tool in C. elegans and not as a therapeutic agent. The compound is stable under standard laboratory storage conditions (powder at -20degC for 3 years). For in vitro assays, Ascr#5 is typically dissolved in appropriate solvents at concentrations ranging from 1 nM to 100 uM.
Toxicity/Toxicokinetics
Toxicological data for Ascr#5 are specific to its role as a nematode pheromone. At physiological concentrations, it regulates development and behavior without causing toxicity to the organism. At supra-physiological concentrations, it may induce excessive dauer formation, which is a developmental arrest state rather than a toxic effect. The compound is not known to be toxic to mammalian cells.
References

[1]. Comparative Ascaroside Profiling of Caenorhabditis Exometabolomes Reveals Species-Specific (ω) and (ω - 2)-Hydroxylation Downstream of Peroxisomal β-Oxidation. J Org Chem. 2018 Jul 6;83(13):7109-7120.

Additional Infomation
Ascr#5 is an ω-hydroxy fatty acid ascaroside, formed by the condensation of the hydroxyl group of 3-hydroxypropionic acid with ascarid pyranose (α-isomer). It is a major component of the diapause pheromone in Caenorhabditis elegans, acting synergistically with ascr#2 and ascr#3 as a population density signal to promote the nematode's entry into another larval stage—a highly prolonged and non-feeding diapause. It is both a pheromone and a metabolite of Caenorhabditis elegans. It is a monocarboxylic acid and an ω-hydroxy fatty acid ascaroside. Functionally, it is related to 3-hydroxypropionic acid. It is the conjugate acid of ascr#5(1-). Ascaroside C3 has been reported to exist in Caenorhabditis elegans, and relevant data are available.
Ascr#5 is a research-use compound not approved for clinical therapeutic applications. It is a critical tool in neurobiology, developmental biology, and chemical ecology research for studying C. elegans development, pheromone signaling, and population density-dependent behaviors. As a purified reference standard, it enables precise investigation of ascaroside-mediated signaling pathways.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C9H16O6
Molecular Weight
220.219743728638
Exact Mass
220.095
CAS #
1086696-26-5
PubChem CID
44202063
Appearance
White to light yellow solid powder
LogP
-1.1
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
4
Heavy Atom Count
15
Complexity
219
Defined Atom Stereocenter Count
4
SMILES
C[C@H]1[C@@H](C[C@H]([C@@H](O1)OCCC(=O)O)O)O
InChi Key
RYYMJVGKZLQYPG-YYWONIAYSA-N
InChi Code
InChI=1S/C9H16O6/c1-5-6(10)4-7(11)9(15-5)14-3-2-8(12)13/h5-7,9-11H,2-4H2,1H3,(H,12,13)/t5-,6+,7+,9+/m0/s1
Chemical Name
3-[(2R,3R,5R,6S)-3,5-dihydroxy-6-methyloxan-2-yl]oxypropanoic acid
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~454.09 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (11.35 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (11.35 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (11.35 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.5409 mL 22.7046 mL 45.4091 mL
5 mM 0.9082 mL 4.5409 mL 9.0818 mL
10 mM 0.4541 mL 2.2705 mL 4.5409 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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