10-Hydroxy-2-decenoic acid CAS 14113-05-4

Introduction：Basic information about 10-Hydroxy-2-decenoic acid CAS 14113-05-4, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

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
• 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)

Safety Information

• Safety Statements: 24/25
• WGK Germany: WGK 3
• HS Code: 29181990
• Storage Class: 11 - Combustible Solids

10-Hydroxy-2-decenoic acid Usage And Synthesis

Description

10-HDA is an unsaturated fatty acid found in royal jelly produced from the hypopharyngeal and mandibular gland secretions of honeybees. 10-HDA has longevity-promoting effects in C. elegans at a concentration of 25 μM. 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. 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.

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].

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.