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

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

Uses

Used in Pharmaceutical Applications:
10-Hydroxy-2-decenoic acid is used as a potential treatment for conditions such as arthritis and rhinitis, due to its anti-inflammatory, anti-bacterial, and anti-tumor properties.
Used in Health Supplements:
10-HDA is used as a health supplement to promote neurological and skin health, as it is believed to have beneficial effects on these areas.
Used in Anti-Aging Products:
10-Hydroxy-2-decenoic acid is used as an ingredient in anti-aging products, as recent studies suggest it may help prevent the effects of aging.
Used in Cosmetics:
10-HDA is used as an ingredient in cosmetics for its potential skin health benefits, contributing to the development of products that aim to improve skin appearance and health.
Used in Agricultural Applications:
10-Hydroxy-2-decenoic acid is used as a natural antibiotic in agricultural applications, potentially serving as an alternative to synthetic antibiotics for promoting the health of livestock and crops.

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

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

Relevant articles and documents

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