Queen bee acid

Last updated
Queen bee acid
Queen Bee Acid.svg
Names
Preferred IUPAC name
(2E)-10-Hydroxydec-2-enoic acid
Other names
  • 10-Hydroxy-2-decenoic acid
  • Royal jelly acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
MeSH C055543
PubChem CID
UNII
  • 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+
    Key: QHBZHVUGQROELI-SOFGYWHQSA-N
  • InChI=1/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+
    Key: QHBZHVUGQROELI-SOFGYWHQBH
  • C(CCC/C=C/C(=O)O)CCCO
Properties
C10H18O3
Molar mass 186.251 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Queen bee acid (10-hydroxy-2-decenoic acid or 10-HDA) is a fatty acid found in royal jelly. [1] [2] [3]

Contents

Queen bee acid is being investigated for its potential pharmacological activities. It promotes neurogenesis of neural stem/progenitor cells (cells capable of differentiating into neurons, astrocytes, or oligodendrocytes) in vitro . [4] In addition, queen bee acid has been reported to have in vitro anti-tumor, anti-biotic, immunomodulatory, estrogenic, neurogenic, and innate immune response modulating activities. [5]

In the United States, the Food and Drug Administration has taken legal action against companies that have used unfounded claims of health benefits to market royal jelly products. [6] [7]

See also

References

  1. ↑ Ji, N; Yu, RG; Yang, QH; Yu, PH; Li, Y (Jul 1987). "[Determination of 10-hydroxy-trans-2-decenoic acid (10-HDA) in royal jelly by gas liquid chromatography]". Zhong Yao Tong Bao. 12 (9): 28–31, 62. PMID   3449246.
  2. ↑ Bloodworth, BC; Harn, CS; Hock, CT; Boon, YO (Jul–Aug 1995). "Liquid chromatographic determination of trans-10-hydroxy-2-decenoic acid content of commercial products containing royal jelly" (PDF). Journal of AOAC International. 78 (4): 1019–23. doi:10.1093/jaoac/78.4.1019. PMID   7580313.
  3. ↑ Genç, Mahmut; Aslan, Abdurrahman (1999). "Determination of trans-10-hydroxy-2-decenoic acid content in pure royal jelly and royal jelly products by column liquid chromatography". Journal of Chromatography A. 839 (1–2): 265–268. doi:10.1016/S0021-9673(99)00151-X. PMID   10327631.
  4. ↑ Hattori, Noriko; Nomoto, Hiroshi; Fukumitsu, Hidefumi; Mishima, Satoshi; Furukawa, Shoei (2007-01-01). "Royal jelly and its unique fatty acid, 10-hydroxy-trans-2-decenoic acid, promote neurogenesis by neural stem/progenitor cells in vitro". Biomedical Research. 28 (5): 261–266. doi: 10.2220/biomedres.28.261 . PMID   18000339.
  5. ↑ Sugiyama, Tsuyoshi; Takahashi, Keita; Mori, Hiroshi (2012). "Royal Jelly Acid, 10-Hydroxy-trans-2-Decenoic Acid, as a Modulator of the Innate Immune Responses". Endocrine, Metabolic & Immune Disorders Drug Targets. 12 (4): 368–376. doi:10.2174/187153012803832530. PMID   23061418.
  6. ↑ "Federal Government Seizes Dozens of Misbranded Drug Products: FDA warned company about making medical claims for bee-derived products". Food and Drug Administration. Apr 5, 2010. Archived from the original on April 7, 2010.
  7. ↑ "Inspections, Compliance, Enforcement, and Criminal Investigations: Beehive Botanicals, Inc". Food and Drug Administration. March 2, 2007. Archived from the original on January 2, 2015.


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