14113-05-4

Basic information

• Product Name: 10-Hydroxy-2-decenoic acid
• Synonyms: HYDROXY-2-DECENOIC ACID, (E)-10-(10-HDA)(P);jelly acid;hydroxy-decenouc 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 NO: 14113-05-4
• Molecular Formula: C₁₀H₁₈O₃
• Molecular Weight: 186.25
• EINECS: 2017-001-1
• Mol File: 14113-05-4.mol
• Article Data: 13

Chemical Properties

• Melting Point: 64.0 to 68.0 °C
• Boiling Point: 339.2 °C at 760 mmHg
• Flash Point: 173.1 °C
• Appearance: /
• Density: 1.038 g/cm³
• Vapor Pressure: 6.5E-06mmHg at 25°C
• Refractive Index: 1.465
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• 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(14113-05-4)
• EPA Substance Registry System: 10-Hydroxy-2-decenoic acid(14113-05-4)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 14113-05-4(Hazardous Substances Data)

Usage

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.

Definition

ChEBI: 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 ro al jelly.

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

(E)-ethyl 10-acetoxydec-2-enoate (1338457-45-6) → (E)-10-hydroxy-dec-2-enoic acid (14113-05-4)

Conditions	Yield
With water; sodium hydroxide In ethanol at 60℃; for 4h;	99.2%

10-hydroxy-dec-2t-enoic acid methyl ester (68750-32-3) → (E)-10-hydroxy-dec-2-enoic acid (14113-05-4)

Conditions	Yield
With sodium hydroxide at 20℃; for 4h; Time;	97%

10-hydroxy 8-decenoic acid ethyl ester (57221-93-9) → (E)-10-hydroxy-dec-2-enoic acid (14113-05-4)

Conditions	Yield
With potassium hydroxide; water In ethanol for 8h;	83%
With potassium hydroxide In ethanol for 1.5h; Heating;	73%
With sodium hydroxide In ethanol for 5h; Heating;	62%
With potassium hydroxide
With potassium hydroxide In ethanol; water at 30℃; for 1h; Yield given;

10-hydroxy-3-decenoic acid (119991-72-9) → (E)-10-hydroxy-dec-2-enoic acid (14113-05-4)

Conditions	Yield
With potassium hydroxide for 3h; Heating;	65%

8-hydroxyoctanal (22054-14-4) + malonic acid (141-82-2) → (E)-10-hydroxy-dec-2-enoic acid (14113-05-4)

Conditions	Yield
With pyridine 1.) ambient temperature, 72 h, 2.) heating on water-bath, 4 h;	61%
With piperidine 1) pyridine, 20 deg C, 16 h, 2) 110 - 115 deg C, 1 h;	49%
With pyridine

malonic acid (141-82-2) + acetic acid 8-oxo-octyl ester (40264-95-7) → (E)-10-hydroxy-dec-2-enoic acid (14113-05-4)

Conditions	Yield
Stage #1: malonic acid; acetic acid 8-oxo-octyl ester With piperidine; pyridine at 22 - 120℃; for 24.5h; Doebner reaction; Stage #2: With potassium carbonate In methanol at 20℃; for 24h;	60%

malonic acid (141-82-2) + 8,8-diethoxy-octan-1-ol (817-45-8) → (E)-10-hydroxy-dec-2-enoic acid (14113-05-4)

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

malonic acid (141-82-2) + Nonane-1,2,9-triol → (E)-10-hydroxy-dec-2-enoic acid (14113-05-4)

Conditions	Yield
(i) aq. KIO4, H2SO4, EtOH, (ii) /BRN= 1751370/, Py; Multistep reaction;

10-acetoxydecanoic acid (92038-37-4) → (E)-10-hydroxy-dec-2-enoic acid (14113-05-4)

Conditions	Yield
(i) SOCl2, (ii) Br2, (iii) NaI, butanone, (iv) KOH, MeOH; Multistep reaction;
Multi-step reaction with 2 steps 1: (i) SOCl2, (ii) Br2, (iii) /BRN= 1098229/, Py 2: (i) NaI, acetone, (ii) KOH, MeOH View Scheme

trans-10-Iod-2-decensaeure (31534-98-2) → (E)-10-hydroxy-dec-2-enoic acid (14113-05-4)

Conditions	Yield
(i) KOAc, AcOH, Py, (ii) KOH; Multistep reaction;

2-Brom-10-acetoxy-decansaeure-methylester (92157-89-6) → (E)-10-hydroxy-dec-2-enoic acid (14113-05-4)

Conditions	Yield
(i) NaI, acetone, (ii) KOH, MeOH; Multistep reaction;

3,10-dihydroxydecanoic acid (762-05-0) → (E)-10-hydroxy-dec-2-enoic acid (14113-05-4)

Conditions	Yield
(i) Ac2O, (ii) KOH, EtOH; Multistep reaction;

Acetic acid 8,10,10,10-tetrachloro-decyl ester → (E)-10-hydroxy-dec-2-enoic acid (14113-05-4)

Conditions	Yield
(i) KOEt, (ii) aq. KOH; Multistep reaction;

8-chloro-1-octanal (72359-96-7) → (E)-10-hydroxy-dec-2-enoic acid (14113-05-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: Py, piperidine 2: NaI / acetone 3: (i) KOAc, AcOH, Py, (ii) KOH View Scheme

trans-10-Chlor-2-decensaeure (31534-97-1) → (E)-10-hydroxy-dec-2-enoic acid (14113-05-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaI / acetone 2: (i) KOAc, AcOH, Py, (ii) KOH View Scheme

2-bromo-9-chloro-nonanoyl chloride → (E)-10-hydroxy-dec-2-enoic acid (14113-05-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: (i) KN3, (ii) (heating), benzene, (iii) KOH 2: Py, piperidine 3: NaI / acetone 4: (i) KOAc, AcOH, Py, (ii) KOH View Scheme

8,8-diethoxy-octanoic acid ethyl ester (26385-59-1) → (E)-10-hydroxy-dec-2-enoic acid (14113-05-4)

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

(E)-8-Oxo-oct-2-enoic acid ethyl ester (26385-57-9) → (E)-10-hydroxy-dec-2-enoic acid (14113-05-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: H2SO4 / ethanol 2: H2 / PtO2 / ethanol 3: LiAlH4 / diethyl ether 4: (i) aq. H2SO4, EtOH, (ii) /BRN= 1751370/ View Scheme

(E)-8,8-Diethoxy-oct-2-enoic acid ethyl ester (26511-33-1) → (E)-10-hydroxy-dec-2-enoic acid (14113-05-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: H2 / PtO2 / ethanol 2: LiAlH4 / diethyl ether 3: (i) aq. H2SO4, EtOH, (ii) /BRN= 1751370/ View Scheme

(2E,4E)-8,8-Diethoxy-octa-2,4-dienoic acid ethyl ester → (E)-10-hydroxy-dec-2-enoic acid (14113-05-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: H2 / PtO2 / 2,2,4-trimethyl-pentane 2: LiAlH4 / diethyl ether 3: (i) aq. H2SO4, EtOH, (ii) /BRN= 1751370/, Py, piperidine View Scheme

1,9-diacetoxynon-1-ene → (E)-10-hydroxy-dec-2-enoic acid (14113-05-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: O3; NaHCO3 / methanol; CH2Cl2 / -70 °C 1.2: 72.4 percent / Me2S; NaHCO3 / methanol; CH2Cl2 / 3 h / -40 - 20 °C 2.1: pyridine; piperidine / 24.5 h / 22 - 120 °C 2.2: 60 percent / K2CO3 / methanol / 24 h / 20 °C View Scheme

(Z)-Cyclooctene (931-88-4, 931-87-3) + hydrogen → (E)-10-hydroxy-dec-2-enoic acid (14113-05-4)

Conditions

Yield

Multi-step reaction with 5 steps 1: 81 percent / mixture of ozone and oxygen (5.5percent masspercent of O3) / acetic acid; cyclohexane 2: 90 percent / TsOH / 16 h / 20 °C 3: 1) DIBAH, 2) water / 1) -10 deg C, toluene, 1.5 h, toluene, THF, 2) 20 deg C, 2 h 4: 97 percent / 10percent HCl / tetrahydrofuran / 16 h / 20 °C 5: 49 percent / piperidine / 1) pyridine, 20 deg C, 16 h, 2) 110 - 115 deg C, 1 h View Scheme

8,8-dimethoxy-octan-1-ol (90661-18-0) → (E)-10-hydroxy-dec-2-enoic acid (14113-05-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 97 percent / 10percent HCl / tetrahydrofuran / 16 h / 20 °C 2: 49 percent / piperidine / 1) pyridine, 20 deg C, 16 h, 2) 110 - 115 deg C, 1 h View Scheme

7-formylheptanoic acid (929-48-6) → (E)-10-hydroxy-dec-2-enoic acid (14113-05-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: 90 percent / TsOH / 16 h / 20 °C 2: 1) DIBAH, 2) water / 1) -10 deg C, toluene, 1.5 h, toluene, THF, 2) 20 deg C, 2 h 3: 97 percent / 10percent HCl / tetrahydrofuran / 16 h / 20 °C 4: 49 percent / piperidine / 1) pyridine, 20 deg C, 16 h, 2) 110 - 115 deg C, 1 h View Scheme

8,8-dimethoxyoctanoic acid methyl ester (65157-89-3) → (E)-10-hydroxy-dec-2-enoic acid (14113-05-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1) DIBAH, 2) water / 1) -10 deg C, toluene, 1.5 h, toluene, THF, 2) 20 deg C, 2 h 2: 97 percent / 10percent HCl / tetrahydrofuran / 16 h / 20 °C 3: 49 percent / piperidine / 1) pyridine, 20 deg C, 16 h, 2) 110 - 115 deg C, 1 h View Scheme

7-Formyl-4Z-heptenoic acid (80685-82-1) → (E)-10-hydroxy-dec-2-enoic acid (14113-05-4)

Conditions	Yield
Multi-step reaction with 5 steps 1: 98 percent / hydrogen / 5percent Pd/C / acetic acid / 15 h / 20 °C / 15200 Torr 2: 90 percent / TsOH / 16 h / 20 °C 3: 1) DIBAH, 2) water / 1) -10 deg C, toluene, 1.5 h, toluene, THF, 2) 20 deg C, 2 h 4: 97 percent / 10percent HCl / tetrahydrofuran / 16 h / 20 °C 5: 49 percent / piperidine / 1) pyridine, 20 deg C, 16 h, 2) 110 - 115 deg C, 1 h View Scheme

8-tetrahydropyranyloxyoctanal (57221-80-4) → (E)-10-hydroxy-dec-2-enoic acid (14113-05-4)

Conditions	Yield
Multi-step reaction with 3 steps 2: 79 percent / p-toluenesulfonic acid / ethanol / 1 h / Heating 3: 73 percent / KOH / ethanol / 1.5 h / Heating View Scheme

ethyl (E)-10-(2-tetrahydropyranyloxy)-2-decenoate (57221-92-8) → (E)-10-hydroxy-dec-2-enoic acid (14113-05-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 79 percent / p-toluenesulfonic acid / ethanol / 1 h / Heating 2: 73 percent / KOH / ethanol / 1.5 h / Heating View Scheme

oct-7-enal (21573-31-9) → (E)-10-hydroxy-dec-2-enoic acid (14113-05-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 65 percent / NaH / hexane; tetrahydrofuran / 3 h / Ambient temperature 2: 1.) 9-borabicyclo<3.3.1>nonane (9-BBN), 2.) aq. NaOH, 30percent aq. H2O2 / 1.) THF, RT, 5 h, 2.) THF, 50 deg C, 1 h 3: 62 percent / aq. NaOH / ethanol / 5 h / Heating View Scheme

(E)-10-hydroxy-dec-2-enoic acid (14113-05-4) + acetic anhydride (108-24-7) → trans-10-acetoxydec-2-enoic acid (68750-29-8)

Conditions	Yield
at 60 - 80℃; for 3h;	97.6%

(E)-10-hydroxy-dec-2-enoic acid (14113-05-4) + propionic acid anhydride (123-62-6) → (E)-10-propionyloxy-2-decenoic acid

Conditions	Yield
at 60 - 80℃; for 3h;	96.1%

diazomethane (186581-53-3, 908094-01-9) + (E)-10-hydroxy-dec-2-enoic acid (14113-05-4) → methyl 9-formyl-(E)-2-nonecate (81550-30-3)

Conditions	Yield
With pyridinium chlorochromate	75%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + (E)-10-hydroxy-dec-2-enoic acid (14113-05-4) → 1-{[(2E)-10-Hydroxydec-2-enoyl]oxy}pyrrolidine-2,5-dione

Conditions	Yield
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 5 - 20℃; for 24h;	52%

(E)-10-hydroxy-dec-2-enoic acid (14113-05-4) → (2E,12E,22E)-triaconta-2,12,22-triene-1,11,21-triolide (128677-37-2) + (2E,12E)-eicosa-2,12-diene-1,11-diolide (83637-48-3) + (3E,14E,25E,36E)-1,12,23,34-Tetraoxa-cyclotetratetraconta-3,14,25,36-tetraene-2,13,24,35-tetraone + C50H80O10

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In benzene at 20℃; for 72h;	A n/a B 24% C n/a D n/a

diazomethane (186581-53-3, 908094-01-9) + (E)-10-hydroxy-dec-2-enoic acid (14113-05-4) → 10-hydroxy-dec-2t-enoic acid methyl ester (68750-32-3)

Upstream product

• 31534-98-2 trans-10-Iod-2-decensaeure 
• 57221-93-9 10-hydroxy 8-decenoic acid ethyl ester 
• 13129-60-7 2-[(5-chloropentyl)oxy]tetrahydropyran 
• 5698-29-3 oxonan-2-one 
• 763-53-1 3-Hydroxy-10-acetoxy-decansaeure-ethylester 
• 819-99-8 3-Keto-10-acetoxy-decansaeure-ethylester 
• 68750-32-3 10-hydroxy-dec-2t-enoic acid methyl ester 
• 10160-24-4 7-bromoheptyl alcohol 
• 141-82-2 malonic acid 
• 1338457-45-6 (E)-ethyl 10-acetoxydec-2-enoate 
• 40646-17-1 8-hydroxyoctan-1-ol acetate 
• 629-41-4 1,8-Octanediol 
• 172759-80-7 (E)-9-formylnon-2-enoic acid 
• 28077-72-7 1-bromo-4-pentyne 

Relevant articles and documents

A new approach to the synthesis of royal jelly acid

A new approach to the synthesis of royal jelly acid (trans-10-hydroxy-2- decenoic acid) was proposed starting from 1,8-octanediol, which included selective monoprotection of 1,8-octanediol with acetic anhydride, oxidation, Wittig-Horner reaction, and hydrolysis and acidification, four steps in total, to yield the product. Overall yield is 80.2%.

Synthesis of 10-hydroxy- and 9-oxo-2E-decenoic acids from oleic acid

A practical synthesis of biologically active 10-hydroxy- and 9-oxo-2E-decenoic acids, components of mandibular gland secretion of honeybee (Apis mellifera L.), is developed using ozonolysis - reduction of oleic acid and 1,9-diacetoxynon-1-ene in the key steps.

LA REACTION DE WITTIG-HORNER EN MILIEU HETEROGENE VI. SELECTIVITE DE LA REACTION SUR DES COMPOSES BIFONCTIONNELS

Heterogenous media of low basicity (K2CO3 or KHCO3), liquid-liquid or solid-liquid allow the Wittig-Horner reaction of fragile and unprotected aldehydes (hydroxyaldehydes, nitroaldehyde and ketoaldehydes) with excellent yields.The reaction is applied to the synthesis of Royal Jelly acid and Queen Substance of Honey bee.

Method for synthesizing royal jelly acid

The invention discloses a method for synthesizing royal jelly acid. 1,8-octanediol from a wide variety of sources, used as a starting material, sequentially undergoes an addition reaction, an oxidation reaction and Knoevenagel reaction-hydrolysis. The method has the advantages of few steps, less byproducts, increase of the yield and reduction of the production cost.

Method for the preparation of unsaturated hydroxy fatty acids and their esters, their use in pharmaceutical and/or cosmetic preparations

A method of preparing unsaturated hydroxy fatty acids and esters thereof corresponding to general formula (Id): wherein n=1 to 4, m=2 to 16, R1═OH, Cl, Br, OR3 in which R3 is a straight or branched alkyl, alkenyl or alkynyl radical of 1 to 16 carbons or glycerol esters, optionally substituted by one or more atoms selected from the group consisting of carbon, nitrogen, sulfur and halogens, R2═H, SiR′1R′2R′3 in which R′1, R′2 and R′3 can be identical or different from each other and are a straight or branched alkyl, alkenyl or alkynyl radical of 1 to 16 carbons or glycerol esters, optionally substituted by one or more atoms selected from the group consisting of carbon, nitrogen, sulfur and halogens, or R2═C—Ar3 with Ar representing an aryl radical optionally substituted by one or more atoms selected from the group consisting of carbon, nitrogen, sulfur and halogens, or R2=the tetrahydropyranyl of formula: is disclosed.