10-Hydroxy-2-decenoic acid CAS#: 14113-05-4; 凯望编码 (ChemWhat Code): 100995

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

英文名10-Hydroxy-2-decenoic acid
IUPAC Name(E)-10-hydroxydec-2-enoic acid  
分子结构10-Hydroxy-2-decenoic-acid-CAS-14113-05-4
CAS编号 14113-05-4
EINECS Number808-119-7
MDL NumberMFCD00204506
别名14113-05-4
10-Hydroxy-2-decenoic acid
10-hydroxydec-2-enoic acid
Royal jelly acid
765-01-5
(E)-10-hydroxydec-2-enoic acid
(E)-10-Hydroxy-2-decenoic acid
Queen Bee Acid
trans-10-Hydroxy-2-decenoic acid
2-Decenoic acid, 10-hydroxy-, (2E)-
10-Hydroxydecenoic acid
10-Hydroxy-2-decylenic acid
10-hydroxy-trans-2-decenoic acid
10-hydroxy-2E-decenoic acid
10-HDA
76B519G7TJ
(2E)-10-hydroxydec-2-enoic acid
NSC-87516
Royaljellyacid
UNII-76B519G7TJ
MFCD00204506
NSC87516
NSC 87516
2-Decenoic acid, 10-hydroxy-, (E)-
Queen Bee Acid;(E)-10-Hydroxy-2-decenoic acid
SCHEMBL285440
10H2DA
CHEBI:78668
10-Hydroxy-2(E)-decenoic acid
QHBZHVUGQROELI-SOFGYWHQSA-N
DTXSID601045504
trans-10-hydroxydec-2-enoic acid
(E)-10-oxidanyldec-2-enoic acid
AMY22616
HY-N1363
10-Hydroxy-2-Decenoic Acid ,(S)
LMFA01050157
s3827
AKOS006282270
AKOS025310134
(2E)-10-Hydroxy-2-decenoic acid #
CCG-266478
10-HYDROXYDECENOIC ACID [INCI]
AC-15652
AC-34577
AS-13924
AS-58742
(E)-10-hydroxydec-2-enoic acid;10-HDA
10-HYDROXY-DEC-(E)-2-ENOIC ACID
CS-0016772
H1337
N-(2,4,6-trichlorophenoxy)ethyl-N-propylamine
O10366
EN300-1704333
A807734
A838726
A865474
J-007465
Q16908844
Z1198152019
分子式C10H18O3 
分子量186.25
InChIInChI=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 Information
Patent IDTitlePublication Date
CN103787879A royal jelly acid derivative and its preparation method and application2016
US2004/204596Method for the preparation of unsaturated hydroxy fatty acids and their esters, their use in pharmaceutical and/or cosmetic preparations2004

Physical Data

AppearanceWhite powder
Melting Point70-75°C
Loss On Drying≤1.0%
Melting Point, °C Solvent (Melting Point)
64 – 65Petroleum ether, diethyl ether
63 – 64diethyl ether, pentane
65 – 66
61.3
62.5 – 63.5diethyl ether
63 – 64CH2Cl2
63 – 65diethyl ether, hexane
Boiling Point, °C
251
250 – 252

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Frequency (NMR Spectroscopy), MHz
Chemical shifts1Hchloroform-d1
Chemical shifts1Hchloroform-d1400
Chemical shifts13Cchloroform-d1100
Chemical shifts, Spectrum1Hchloroform-d1
Description (IR Spectroscopy)Temperature (IR Spectroscopy), °C
Bands
Bandsneat (no solvent)
BandsKBr
Description (UV/VIS Spectroscopy)
Absorption maxima

Route of Synthesis (ROS)

Route of Synthesis (ROS) of 10-Hydroxy-2-decenoic acid

Route of Synthesis (ROS) of 10-Hydroxy-2-decenoic acid

ConditionsYield
With potassium hydroxide; water In ethanol for 8h;

Experimental Procedure

119.6 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%). [0075] Characterization [0076] TLC: Rf=0.2 (heptane/ethyl acetate 7/3) [0077] Melting point: mp=61.3° C. [0078] 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)exclamation-mark
SignalWarning
GHS Hazard StatementsH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/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 Code
StorageStore at room temperature for long time, in container tightly sealed; Protect from light.
Shelf Life3 year
Market Price
Druglikeness
Lipinski rules component
分子量186.251
logP2.28
HBA3
HBD2
Matching Lipinski Rules4
Veber rules component
Polar Surface Area (PSA)57.53
Rotatable Bond (RotB)8
Matching Veber Rules2
Quantitative Results
1 of 58Comment (Pharmacological Data)Bioactivities present
Reference
2 of 58 Comment (Pharmacological Data)Bioactivities present
ReferenceLA REACTION DE WITTIG-HORNER EN MILIEU HETEROGENE VI. SELECTIVITE DE LA REACTION SUR DES COMPOSES BIFONCTIONNELS
3 of 58 Comment (Pharmacological Data)Bioactivities present
ReferenceThe Physiology of Caste Development in Social Insects
4 of 58Comment (Pharmacological Data)Bioactivities present
ReferenceRoyalactin extends lifespan of Caenorhabditis elegans through epidermal growth factor signaling
5 of 58 Comment (Pharmacological Data)Bioactivities present
ReferenceThe 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 Pattern
10-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.

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