Details
Stereochemistry | ACHIRAL |
Molecular Formula | C10H18O3 |
Molecular Weight | 186.2481 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OCCCCCCC\C=C\C(O)=O
InChI
InChIKey=QHBZHVUGQROELI-SOFGYWHQSA-N
InChI=1S/C10H18O3/c11-9-7-5-3-1-2-4-6-8-10(12)13/h6,8,11H,1-5,7,9H2,(H,12,13)/b8-6+
Molecular Formula | C10H18O3 |
Molecular Weight | 186.2481 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/28701955Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/23563566 | https://www.ncbi.nlm.nih.gov/pubmed/21948282 | https://www.ncbi.nlm.nih.gov/pubmed/21348496 | https://www.ncbi.nlm.nih.gov/pubmed/28740028
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28701955
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/23563566 | https://www.ncbi.nlm.nih.gov/pubmed/21948282 | https://www.ncbi.nlm.nih.gov/pubmed/21348496 | https://www.ncbi.nlm.nih.gov/pubmed/28740028
10-Hydroxy-2-decenoic acid, a natural fatty acid that has been extracted from royal jelly obtained from honeybees (Apis mellifera) and exhibits estrogenic action. 10-hydroxy-2-decenoic(10-HDA)dose-dependently inhibited the formation of the gastric ulcer induced by stress, pyloric ligation, and indomethacin selectively in rats. 10-HDA also accelerated the healing of gastric ulcer induced by acetic acid, by which the gastric acid output was decreased in a dose-dependent manner. A mechanism putatively linked to 10-HDA anti-inflammatory effect is the inhibition of LPS-induced NF-kB activation observed in the murine macrophage cell line RAW264. 10-HDA and 4-hydroperoxy-2-decenoic acid ethyl ester have been shown to inhibit histone deacetylase activity, thereby enhancing the expression of extracellular SOD release by leukemia THP-1 cells, and suggesting therapeutic potential against atherosclerosis. Various immunomodulatory activities have been reported for 10-HDA, including reduced T cell proliferation, inhibition of interleukin-12 production by spleen dendritic cells, and blocks of LPS- and IFN-b-induced NO production in macrophages. 10-HDA has been shown to increase collagen synthesis and production of the collagen promoting factor, transforming growth factor b1, in human skin fibroblasts. Such an effect is thought to mediate royal jelly skin protection against UVB-induced photoaging. 10-HDA and 10-hydroxydecanoic acid have been shown to act as potent agonists of the human TRPA1 and TRPV1 receptors. 10-HDA has stimulated neuron differentiation from rat embryo neural stem cells, possibly acting like the omega-3 docosahexaenoic acid, an essential diet component that is known to promote neurogenesis in the central nervous system.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: GO:0038061 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21948282 |
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Target ID: CHEMBL6007 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21348496 |
422.0 µM [EC50] | ||
Target ID: CHEMBL4794 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21348496 |
850.0 µM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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[Features of fatty acid composition of queen bee jelly]. | 2001 |
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Antifatigue effect of fresh royal jelly in mice. | 2001 Dec |
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Storage-dependent degradation of 57-kDa protein in royal jelly: a possible marker for freshness. | 2001 Feb |
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[The research of 10-hydroxy-2-decenoic acid on experiment hyperlipoidemic rat]. | 2002 May |
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Insight into some of the signaling pathways triggered by a lipid immunomodulator. | 2002 Nov |
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Identification of a collagen production-promoting factor from an extract of royal jelly and its possible mechanism. | 2004 Apr |
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Isolation and characterization of some hydroxy fatty and phosphoric acid esters of 10-hydroxy-2-decenoic acid from the royal jelly of honeybees (Apis mellifera). | 2005 Aug |
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Royal jelly prevents osteoporosis in rats: beneficial effects in ovariectomy model and in bone tissue culture model. | 2006 Sep |
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Understanding the logics of pheromone processing in the honeybee brain: from labeled-lines to across-fiber patterns. | 2007 |
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Evaluation of the immunomodulatory activities of royal jelly components in vitro. | 2007 |
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Optimized determination method for trans-10-hydroxy-2-decenoic acid content in royal jelly by high-performance liquid chromatography with an internal standard. | 2007 Jan-Feb |
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Determination of (E)-10-hydroxy-2-decenoic acid content in pure royal jelly: a comparison between a new CZE method and HPLC. | 2007 May |
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Royal jelly and its unique fatty acid, 10-hydroxy-trans-2-decenoic acid, promote neurogenesis by neural stem/progenitor cells in vitro. | 2007 Oct |
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Compositions of royal jelly II. Organic acid glycosides and sterols of the royal jelly of honeybees (Apis mellifera). | 2007 Oct |
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Estrogenic activities of Fatty acids and a sterol isolated from royal jelly. | 2008 Sep |
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10-Hydroxy-2-decenoic acid, a major fatty acid from royal jelly, inhibits VEGF-induced angiogenesis in human umbilical vein endothelial cells. | 2009 Dec |
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Comparison of bee products based on assays of antioxidant capacities. | 2009 Feb 26 |
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Drones of the dwarf honey bee Apis florea are attracted to (2E)-9-oxodecenoic acid and (2E)-10-hydroxydecenoic acid. | 2009 Jun |
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Bee products prevent VEGF-induced angiogenesis in human umbilical vein endothelial cells. | 2009 Nov 17 |
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Fatty acids derived from royal jelly are modulators of estrogen receptor functions. | 2010 Dec 22 |
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10-Hydroxy-2-decenoic acid from Royal jelly: a potential medicine for RA. | 2010 Mar 24 |
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Effect of royal jelly on experimental colitis Induced by acetic acid and alteration of mast cell distribution in the colon of rats. | 2010 Oct 21 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28740028
Mice were treated with 10-Hydroxy-2-decenoic acid (3 mg/kg body weight) for 4 weeks by oral gavage
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21948282
The RAW264 murine macrophage cell line was obtained from RIKEN Bioresource Center (Tokyo, Japan) and maintained in RPMI-1640 medium containing 5% heat-mactivated fetal bovine serum. Cells were seeded in a 96-well plate at 2 x 10^5 cells/well for NO and cytokine assays and 5 x 10^4 cells/well for the reporter gene assay Cells were preincubated with or without the indicated concentrations (up to 5 mM) of 10HDA for 30 mm, and then stimulated by adding LPS or IFN-p for the indicated periods.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:46:59 GMT 2023
by
admin
on
Fri Dec 15 19:46:59 GMT 2023
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Record UNII |
76B519G7TJ
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Record Status |
Validated (UNII)
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Record Version |
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DTXSID50997870
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87516
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765-01-5
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76B519G7TJ
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Queen_bee_acid
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14113-05-4
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