| Identification | Back Directory | [Name]
2-Nonenoic acid, 8-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]-, (2E,8R)- | [CAS]
946524-26-1 | [Synonyms]
Ascr#3
2-Nonenoic acid, 8-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]-, (2E,8R)- | [Molecular Formula]
C15H26O6 | [MDL Number]
MFCD28010961 | [MOL File]
946524-26-1.mol | [Molecular Weight]
302.37 |
| Chemical Properties | Back Directory | [Boiling point ]
513.0±50.0 °C(Predicted) | [density ]
1.18±0.1 g/cm3(Predicted) | [storage temp. ]
4°C, protect from light | [solubility ]
Soluble in DMSO | [form ]
Oil | [pka]
4.78±0.10(Predicted) | [color ]
Colorless to light yellow |
| Hazard Information | Back Directory | [Uses]
Ascr#3 is a type of pheromone found in the beautiful nematode, and when mixed with ascr#2, it can act as a male attractant and also induce the formation of dauer (the dormant larval stage). Ascr#3 can counteract the effects caused by male-enriched Ascr#10[1][2]. | [Definition]
ChEBI: Ascr#3 is an (omega-1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E,8R)-8-hydroxynon-2-enoic acid with ascarylopyranose (the alpha anomer). It is a major component of the dauer pheromone, used by the nematode Caenorhabditis elegans as a population-density signal to promote entry into an alternate larval stage, the nonfeeding and highly persistent dauer diapause, and also synergises with ascr#2, ascr#4, and ascr#8 in male attraction. It has a role as a Caenorhabditis elegans metabolite and a pheromone. It is an alpha,beta-unsaturated monocarboxylic acid and an (omega-1)-hydroxy fatty acid ascaroside. It is functionally related to a (2E,8R)-8-hydroxynon-2-enoic acid. It is a conjugate acid of an ascr#3(1-). | [in vivo]
Ascr#3 acts as a powerful male attractant at very low concentrations, but when the concentration increases enough to induce larvae into the dauer stage, Ascr#3 no longer attracts males and instead repels hermaphrodites[1].
Ascr#3 is perceived through the mediation of both sex-specific and general sensory neurons[1]. | [References]
[1] Srinivasan J, et al. A blend of small molecules regulates both mating and development in Caenorhabditis elegans. Nature. 2008 Aug 28;454(7208):1115-8. DOI:10.1038/nature07168
[2] Erin Z Aprison, et al. Counteracting Ascarosides Act through Distinct Neurons to Determine the Sexual Identity of C. elegans Pheromones. Curr Biol. 2017 Sep 11;27(17):2589-2599.e3. DOI:10.1016/j.cub.2017.07.034 |
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