IdentificationPhysical DataSpectraRoute of Synthesis (ROS)Safety and HazardsOther Data
Identification
Product Name10-Hydroxy-2-decenoic acidIUPAC Name(E)-10-hydroxydec-2-enoic acid Molecular StructureCAS Registry Number 14113-05-4EINECS Number808-119-7MDL NumberMFCD00204506Synonyms14113-05-410-Hydroxy-2-decenoic acid10-hydroxydec-2-enoic acidRoyal jelly acid765-01-5(E)-10-hydroxydec-2-enoic acid(E)-10-Hydroxy-2-decenoic acidQueen Bee Acidtrans-10-Hydroxy-2-decenoic acid2-Decenoic acid, 10-hydroxy-, (2E)-10-Hydroxydecenoic acid10-Hydroxy-2-decylenic acid10-hydroxy-trans-2-decenoic acid10-hydroxy-2E-decenoic acid10-HDA76B519G7TJ(2E)-10-hydroxydec-2-enoic acidNSC-87516RoyaljellyacidUNII-76B519G7TJMFCD00204506NSC87516NSC 875162-Decenoic acid, 10-hydroxy-, (E)-Queen Bee Acid;(E)-10-Hydroxy-2-decenoic acidSCHEMBL28544010H2DACHEBI:7866810-Hydroxy-2(E)-decenoic acidQHBZHVUGQROELI-SOFGYWHQSA-NDTXSID601045504trans-10-hydroxydec-2-enoic acid(E)-10-oxidanyldec-2-enoic acidAMY22616HY-N136310-Hydroxy-2-Decenoic Acid ,(S)LMFA01050157s3827AKOS006282270AKOS025310134(2E)-10-Hydroxy-2-decenoic acid #CCG-26647810-HYDROXYDECENOIC ACID AC-15652AC-34577AS-13924AS-58742(E)-10-hydroxydec-2-enoic acid;10-HDA10-HYDROXY-DEC-(E)-2-ENOIC ACIDCS-0016772H1337N-(2,4,6-trichlorophenoxy)ethyl-N-propylamineO10366EN300-1704333A807734A838726A865474J-007465Q16908844Z1198152019Molecular FormulaC10H18O3 Molecular Weight186.25InChIInChI=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+ InChI KeyQHBZHVUGQROELI-SOFGYWHQSA-N Isomeric SMILESC(CCC/C=C/C(=O)O)CCCO
Patent InformationPatent IDTitlePublication DateCN103787879A royal jelly acid derivative and its preparation method and application2016US2004/204596Method for the preparation of unsaturated hydroxy fatty acids and their esters, their use in pharmaceutical and/or cosmetic preparations2004
Physical Data
AppearanceWhite powderMelting Point70-75°CLoss On Drying≤1.0%
Melting Point, °C Solvent (Melting Point) 64 - 65Petroleum ether, diethyl ether63 - 64diethyl ether, pentane65 - 6661.362.5 - 63.5diethyl ether63 - 64CH2Cl263 - 65diethyl ether, hexane
Boiling Point, °C251250 - 252
Spectra
Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Frequency (NMR Spectroscopy), MHzChemical shifts1Hchloroform-d1Chemical shifts1Hchloroform-d1400Chemical shifts13Cchloroform-d1100Chemical shifts, Spectrum1Hchloroform-d1
Description (IR Spectroscopy)Temperature (IR Spectroscopy), °CBandsBandsneat (no solvent)BandsKBr
Description (UV/VIS Spectroscopy)Absorption maxima
Route of Synthesis (ROS)
Route of Synthesis (ROS) of 10-Hydroxy-2-decenoic acid
ConditionsYieldWith potassium hydroxide; water In ethanol for 8h;Experimental Procedure119.6 g (0.56 mol) of hydroxyester was dissolved in 600 ml of ethanol and 400 ml of a 4.6 N solution of KOH was added. The medium was agitated for 8 h. The medium was extracted with isopropyl ether. The aqueous phase was acidified to pH=1 and extracted with ethyl acetate. After drying and evaporation, 99.6 g of pink solids were obtained. The solids were recrystallized in an isopropyl ether/petroleum ether mixture. The product was obtained in the form of a white solid (86 g, 83%). Characterization TLC: Rf=0.2 (heptane/ethyl acetate 7/3) Melting point: mp=61.3° C. 1H NMR (400 MHz, CDCl3): 7.06 (dt, 1H, J=15.6 and 7 Hz); 5.81 (dt, 1H, J=1.5 and 15.6 Hz); 3.64 (t, 2H, J=6.6 Hz); 2.22 (dq, 2H, J=1.2 and 7.3 Hz); 1.52-1.58 (m, 2H); 1.45-1.48 (m, 2H); 1.33-1.3765 (m, 6H).83%With potassium hydroxide In ethanol for 1.5h; Heating;73%With sodium hydroxide In ethanol for 5h; Heating;62%
Safety and Hazards
Pictogram(s)SignalWarningGHS Hazard StatementsH315 (100%): Causes skin irritation H319 (100%): Causes serious eye irritation Precautionary Statement CodesP264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364(The corresponding statement to each P-code can be found at the GHS Classification page.)
Other Data
Store at room temperature for long time, in container tightly sealed; Protect from light.HS CodeStorageStore at room temperature for long time, in container tightly sealed; Protect from light.Shelf Life3 yearMarket Price
DruglikenessLipinski rules componentMolecular Weight186.251logP2.28HBA3HBD2Matching Lipinski Rules4Veber rules componentPolar Surface Area (PSA)57.53Rotatable Bond (RotB)8Matching Veber Rules2
Quantitative Results1 of 58Comment (Pharmacological Data)Bioactivities presentReference2 of 58 Comment (Pharmacological Data)Bioactivities presentReferenceLA REACTION DE WITTIG-HORNER EN MILIEU HETEROGENE VI. SELECTIVITE DE LA REACTION SUR DES COMPOSES BIFONCTIONNELS3 of 58 Comment (Pharmacological Data)Bioactivities presentReferenceThe Physiology of Caste Development in Social Insects4 of 58Comment (Pharmacological Data)Bioactivities presentReferenceRoyalactin extends lifespan of Caenorhabditis elegans through epidermal growth factor signaling5 of 58 Comment (Pharmacological Data)Bioactivities presentReferenceThe influence of royal jelly and human interferon-alpha (HuIFN-αN3) on proliferation, glutathione level and lipid peroxidation in human colorectal adenocarcinoma cells in vitro
Use Pattern10-Hydroxy-2-decenoic acid possesses antioxidant properties, helping to combat the damage caused by free radicals and maintaining cellular health. And It is believed to have anti-inflammatory characteristics and can be used to alleviate inflammation-related health issues.
https://www.chemwhat.com/10-hydroxy-2-decenoic-acid-cas-14113-05-4/
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