| Identification | More | [Name]
10-Hydroxy-2-decenoic acid | [CAS]
14113-05-4 | [Synonyms]
10-HAD
10-HDA
10-HYDROXY-2-DECENOIC ACID
10-HYDROXY-2-(E)-DECENOIC ACID
10-HYDROXY-2TR-DECENOIC ACID
10-HYDROXYDECENOIC ACID
(E)-10-HYDROXY-2-DECENOIC ACID
HYDROXY-2-DECENOIC ACID, (E)-10-
OMEGA-HYDROXY C10:1 (2-TRANS)
QUEEN BEE ACID
ROYAL JELLY ACID
10-HYDROXY-2-DECENOIC ACID (10-HAD)
10-Hydroxy-2tr-Decenoic?Acid?(Royal?Jelly?Acid)?
10-HYDROXY-2-DECENOIC ACID (10HDA)
HYDROXY-2-DECENOIC ACID, (E)-10-(10-HDA)(SH)
10-Hydroxydecylenic acid
ω-Hydroxy-Δ2-decenoic acid
10-Hydroxy-2-decenoic acid | [EINECS(EC#)]
808-119-7 | [Molecular Formula]
C10H18O3 | [MDL Number]
MFCD00204506 | [Molecular Weight]
186.25 | [MOL File]
14113-05-4.mol |
| Chemical Properties | Back Directory | [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. ]
Inert atmosphere,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 | [Major Application]
food and beverages | [InChI]
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+ | [InChIKey]
QHBZHVUGQROELI-SOFGYWHQSA-N | [SMILES]
C(O)(=O)/C=C/CCCCCCCO | [LogP]
1.808 (est) | [CAS DataBase Reference]
14113-05-4(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Description]
10-HDA is an unsaturated fatty acid found in royal jelly produced from the hypopharyngeal and mandibular gland secretions of honeybees.1 10-HDA has longevity-promoting effects in C. elegans at a concentration of 25 μM.2 It down-regulates matrix metalloproteinases (MMPs) in rheumatoid arthritis synovial fibroblasts at a concentration of 1.25 nM and inhibits VEGF-induced angiogenesis in HUVECs at 500 μM.3,4 10-HDA also facilitates differentiation of neurons from neural stem/progenitor cells and promotes collagen production by skin fibroblasts at concentrations of 100 μM and 1.5 mM, respectively.5,6 | [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: 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 ro
al jelly. | [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].
| [in vivo]
Royal Jelly Acid (3-6 mg/kg, p.o., once daily for 25 days) significantly inhibits disease progression, reduces inflammatory cell infiltration, and prevents demyelination in the MOG35-55-induced experimental autoimmune encephalomyelitis C57BL/6 mouse model [6]. | Animal Model: | MOG35–55-induced experimental autoimmune encephalomyelitis (EAE) C57BL/6 mouse model[6] | | Dosage: | 3 mg/kg (low dose) or 6 mg/kg (high dose) | | Administration: | Oral gavage (p.o.), once daily for 25 days | | Result: | Reduced EAE scores, prevented body weight loss, and decreased leukocyte infiltration and demyelination in the CNS. |
| [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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