765-01-5

Basic information

• Product Name: 10-Hydroxy-2-decenoic acid
• Synonyms: (E)-10-HYDROXY-2-DECENOIC ACID;HYDROXY-2-DECENOIC ACID, (E)-10-;10-HYDROXYDECENOIC ACID;10-HYDROXY-2-(E)-DECENOIC ACID;10-HYDROXY-2TR-DECENOIC ACID;10-HAD;10-HDA;ROYAL JELLY ACID
• CAS NO: 765-01-5
• Molecular Formula: C₁₀H₁₈O₃
• Molecular Weight: 186.25
• EINECS: 1592732-453-0
• Product Categories: Miscellaneous Natural Products
• Mol File: 765-01-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 55 °C
• Boiling Point: 339.2 °C at 760 mmHg
• Flash Point: 173.1 °C
• Appearance: White or type of white crystals
• Density: 1.038 g/cm³
• Vapor Pressure: 6.5E-06mmHg at 25°C
• Refractive Index: 1.465
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 4.78±0.10(Predicted)
• CAS DataBase Reference: 10-Hydroxy-2-decenoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 10-Hydroxy-2-decenoic acid(765-01-5)
• EPA Substance Registry System: 10-Hydroxy-2-decenoic acid(765-01-5)

Safety Data

• Hazardous Substances Data: 765-01-5(Hazardous Substances Data)

Usage

General Description

10-Hydroxy-2-decenoic acid, often abbreviated as 10-HDA, is a bio-active compound and the primary fatty acid found in royal jelly, the exclusive nutrient source for queen bees. This chemical is known for its antibiotic properties and potential health benefits. It's considered a potential treatment for conditions such as arthritis and rhinitis, and shows potential as an anti-inflammatory, anti-bacterial, and anti-tumor agent. Furthermore, 10-HDA is believed to promote neurological and skin health, and recent studies suggest it may help prevent the effects of aging. Despite its potential benefits, more research is needed to fully understand its properties and applications.

InChI:InChI=1/C11H22O3/c1-10(11(13)14)8-6-4-2-3-5-7-9-12/h10,12H,2-9H2,1H3,(H,13,14)

Synthetic route

C10H17BrO2 → 10-hydroxy-2-decenoic acid (765-01-5)

Conditions	Yield
Stage #1: C10H17BrO2 With sodium hydroxide In ethanol at 20℃; for 3h; Stage #2: With hydrogenchloride In water pH=4; Time;	97%

C12H22O3 (64971-15-9) → 10-hydroxy-2-decenoic acid (765-01-5)

Conditions	Yield
Stage #1: C12H22O3 With sodium carbonate In tetrahydrofuran; water at 65℃; for 3h; Stage #2: With hydrogenchloride; water In tetrahydrofuran pH=2;	71%
With sodium carbonate In tetrahydrofuran at 65℃; for 3h;

malonic acid (141-82-2) + 8,8-diethoxy-octan-1-ol (817-45-8) → 10-hydroxy-2-decenoic acid (765-01-5)

Conditions	Yield
(i) aq. H2SO4, MeOH, (ii) /BRN= 1751370/, Py; Multistep reaction;

10-hydroxy 8-decenoic acid ethyl ester (57221-93-9) → 10-hydroxy-2-decenoic acid (765-01-5)

Conditions	Yield
With potassium hydroxide In ethanol for 0.5h; Heating; Yield given;

8-hydroxyoctanal (22054-14-4) → 10-hydroxy-2-decenoic acid (765-01-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. potassium carbonate / 1 h 2: potassium hydroxide / aq. ethanol / 0.5 h / Heating View Scheme

1-ethoxy 10-methyl 9,11-dioxa 1-tridecene → 10-hydroxy-2-decenoic acid (765-01-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. hydrochloric acid / acetone / 2 h / 0 °C 2: aq. potassium carbonate / 1 h 3: potassium hydroxide / aq. ethanol / 0.5 h / Heating View Scheme

cycloactanone (502-49-8) → 10-hydroxy-2-decenoic acid (765-01-5)

Conditions	Yield
Multi-step reaction with 3 steps 2: LiAlH4 / diethyl ether 3: (i) aq. H2SO4, MeOH, (ii) /BRN= 1751370/, Py View Scheme

8,8-diethoxy-octanoic acid ethyl ester (26385-59-1) → 10-hydroxy-2-decenoic acid (765-01-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4 / diethyl ether 2: (i) aq. H2SO4, MeOH, (ii) /BRN= 1751370/, Py View Scheme

oxonan-2-one (5698-29-3) → 10-hydroxy-2-decenoic acid (765-01-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere 2: potassium carbonate / ethanol / 18 h / 40 °C 3: sodium carbonate / tetrahydrofuran / 3 h / 65 °C View Scheme

N-(methyl)-N-(p-toluenesulfonyl)ethynylamine (1005500-75-3) + 10-hydroxy-2-decenoic acid (765-01-5) → C20H29NO5S

Conditions	Yield
In dichloromethane at 20℃;	98%
With copper(l) chloride In dichloromethane at 20℃; for 4h;	91%

10-hydroxy-2-decenoic acid (765-01-5) + 1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7) → C11H15N2O5(1+)*C10H17O3(1-)*C10H18O3

Conditions	Yield
In methanol at -10 - -5℃; for 2h; Inert atmosphere;	50%

10-hydroxy-2-decenoic acid (765-01-5) + 2-amino-2-hydroxymethyl-1,3-propanediol (77-86-1) → 10-hydroxydec-2-enoic acid 3-hydroxy-2-(10-hydroxydec-2-enoylamino)-2-hydroxymethylpropyl ester

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 6.5h;	39%

10-hydroxy-2-decenoic acid (765-01-5) + phenethylamine (64-04-0) → C29H49NO2Si + C29H49NO2Si

Conditions	Yield
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 12 h / 20 °C 2: [Ir(1,5-cyclooctadiene)2]triflate; (R)-(+)-(4,4'-bi-1,3-benzodioxole)-5,5'-diylbis(di(3,5-dimethylphenyl)phosphine) / tetrahydrofuran / 12 h / 40 °C / Inert atmosphere; Glovebox View Scheme

10-hydroxy-2-decenoic acid (765-01-5) + phenethylamine (64-04-0) → C18H27NO2

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h;

10-hydroxy-2-decenoic acid (765-01-5) + ascorbic acid (50-81-7) → C16H24O8

Conditions	Yield
With thionyl chloride; triethylamine In dichloromethane Inert atmosphere;

10-hydroxy-2-decenoic acid (765-01-5) + C11H15N2O5(1+)*C4H5O5(1-)*C4H6O5 → C4H5O5(1-)*C4H6O5*(x)C10H17O3(1-)*C11H15N2O5(1+)

Conditions	Yield
for 0.166667h; Inert atmosphere;	7.05 g

10-hydroxy-2-decenoic acid (765-01-5) → C10H16O2

Conditions	Yield
Multi-step reaction with 2 steps 1: dichloromethane / 20 °C 2: toluene-4-sulfonic acid / dichloromethane / 20 °C View Scheme

Upstream product

• 26385-59-1 8,8-diethoxy-octanoic acid ethyl ester 
• 5698-29-3 oxonan-2-one 
• 64971-15-9 C₁₂H₂₂O₃ 
• 502-49-8 cycloactanone 
• 22054-14-4 8-hydroxyoctanal 
• 57221-93-9 10-hydroxy 8-decenoic acid ethyl ester 
• 141-82-2 malonic acid 
• 817-45-8 8,8-diethoxy-octan-1-ol 

Relevant articles and documents

Preparation method of royal jelly acid

The invention discloses a preparation method of royal jelly acid, and belongs to the field of chemical synthesis. The preparation method comprises the following steps: taking 1, 10-decanediol as a rawmaterial, taking water as a solvent, and under the action of potassium persulfate and tetraalkyl ammonium bromide, preparing a 2-bromodecalactone (II) compound, wherein the reaction adopts an one-potmethod to carry out three step reactions of oxidation, lactonization and alpha-H bromination respectively, and has relatively high selectivity and yield; and carrying out hydrolysis and elimination reaction on the 2-bromodecalactone (II) compound, and finally carrying out acidifying to obtain a royal jelly acid target product; the purity of a crude product can reach 95%, and the purity of the product reaches more than 99% after recrystallization. According to the method, the royal jelly acid is prepared by adopting two steps, and the preparation method has the advantages of short route and simplicity and convenience in operation, is easy for industrial production, and is a method for synthesizing the royal jelly acid very economically and simply.

Novel Method for Preparing Unsaturated Fatty Hydroxyacids

The invention concerns a method for preparing a compound of formula (I), wherein: R3 and R1 represent in particular H and n is greater than 4, said preparation method including performing a Wittig-Horner reaction with a phosphonate on a lactol, so as to obtain a hydroxyester and, optionally a saponification reaction of said hydroxyester.