10-Hydroxy-2-decenoic acid
10-Hydroxy-2-decenoic acid Basic information
- Product Name:
- 10-Hydroxy-2-decenoic acid
- Synonyms:
-
- HYDROXY-2-DECENOIC ACID, (E)-10-(10-HDA)(P)
- hydroxy-decenouc acid
- jelly acid
- trans-10-Hydroxy-2-decenoic Acid
- (E)-10-hydroxydec-2-enoic acid
- Queen been acid
- 10-HAD,10-hydroxydec-2-enoic acid
- OMEGA-HYDROXY C10:1 (2-TRANS)
- CAS:
- 14113-05-4
- MF:
- C10H18O3
- MW:
- 186.25
- EINECS:
- 808-119-7
- Product Categories:
-
- 1
- Mol File:
- 14113-05-4.mol
10-Hydroxy-2-decenoic acid Chemical Properties
- Melting point:
- 64.0 to 68.0 °C
- Boiling point:
- 339.2±15.0 °C(Predicted)
- Density
- 1.038±0.06 g/cm3(Predicted)
- storage temp.
- under inert gas (nitrogen or Argon) at 2-8°C
- solubility
- DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 20 mg/ml
- form
- powder to crystal
- pka
- 4.78±0.10(Predicted)
- color
- White to Almost white
- LogP
- 1.808 (est)
- CAS DataBase Reference
- 14113-05-4(CAS DataBase Reference)
Safety Information
- Safety Statements
- 24/25
- HS Code
- 29181990
10-Hydroxy-2-decenoic acid Usage And Synthesis
Description
10-
Uses
10-Hydroxy-2-decenoic acid has antiseptic, anti-inflammatory, anti-obesity, anti-aging, preventing bone loss and anti-tumour pharmacological effects, with potential therapeutic effects for postmenopausal osteoporosis, as well as benefiting the human gastrointestinal tract[1-3].
Definition
ChEBI: (E)-10-hydroxydec-2-enoic acid is an omega-hydroxy amino acid that is 2-decenoic acid in which one of the hydrogens attached to the terminal carbon is replaced by a hydroxy group and in which the C=C double bond has E configuration. It is a component of royal jelly. It has a role as an animal metabolite and a geroprotector. It is an alpha,beta-unsaturated monocarboxylic acid, a straight-chain fatty acid, a hydroxy monounsaturated fatty acid and an omega-hydroxy-medium-chain fatty acid.
Biological Activity
10-Hydroxy-2-decenoic acid is an orally available royal jelly component that potently inhibits osteoclastogenesis. It binds to free fatty acid receptor 4 (FFAR4) on osteoclasts which inhibits RANKL (receptor activator of nuclear factor-κB (NF-κB) ligand), thereby attenuating the induction of nuclear factor of activated T cells (NFAT) c1. 10-Hydroxy-2-decenoic acid inhibits bone resorption in ovariectomized mice.
The production of pro-inflammatory cytokines, Interleukin (IL)-8, IL-1β and tumor necrosis factor-alpha (TNF-α) in WiDr cells was modulated by 10-HDA. IL-8 were dramatically declined by 10-HDA at 3 mM, while IL-1β and TNF-α were significantly decreased. 10-HDA increased IL-1ra in a dose manner. NF-κB pathway is primarily in response to prototypical pro-inflammatory cytokines, and NF-κB was reduced after 10-HDA treatment. 10-HDA acted as potent bactericide against animal- or human-specific pathogens, including Staphylococcus aureus, Streptococcus alactolyticus, Staphylococcus intermedius B, Staphylococcus xylosus, Salmonella cholearasuis, Vibro parahaemolyticus and Escherichia coli (hemolytic)[1].
References
[1] YUAN-CHANG YANG. 10-hydroxy-2-decenoic acid of royal jelly exhibits bactericide and anti-inflammatory activity in human colon cancer cells.[J]. BMC Complementary and Alternative Medicine, 2018: 202. DOI:10.1186/s12906-018-2267-9.
[2] YOKO HONDA. 10-Hydroxy-2-decenoic Acid, the Major Lipid Component of Royal Jelly, Extends the Lifespan of Caenorhabditis elegans through Dietary Restriction and Target of Rapamycin Signaling.[J]. Journal of Aging Research, 2015, 2015: 425261. DOI:10.1155/2015/425261.
[3] YOSUKE TSUCHIYA. The key royal jelly component 10-hydroxy-2-decenoic acid protects against bone loss by inhibiting NF-κB signaling downstream of FFAR4.[J]. The Journal of Biological Chemistry, 2020, 295 34: 12224-12232. DOI:10.1074/jbc.RA120.013821.
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