Product Name

  • Name

    10-Hydroxy-2-decenoic acid

  • EINECS 808-119-7
  • CAS No. 14113-05-4
  • Article Data31
  • CAS DataBase
  • Density 1.038 g/cm3
  • Solubility
  • Melting Point 64.0 to 68.0 °C
  • Formula C10H18O3
  • Boiling Point 339.2 °C at 760 mmHg
  • Molecular Weight 186.251
  • Flash Point 173.1 °C
  • Transport Information
  • Appearance
  • Safety 24/25
  • Risk Codes
  • Molecular Structure Molecular Structure of 14113-05-4 (10-Hydroxy-2-decenoic acid)
  • Hazard Symbols
  • Synonyms 2-Decenoic acid,10-hydroxy-, (2E)-;(E)-10-Hydroxydecenoic acid;10-Hydroxy-2E-decenoic acid;10-Hydroxy-trans-2-decenoic acid;Biosil;NSC 87516;trans-10-Hydroxy-2-decenoic acid;2-Decenoicacid, 10-hydroxy-, (E)- (8CI);Royal jelly acid (6CI);2-Decenoic acid,10-hydroxy-, trans- (6CI);(E)-10-Hydroxy-2-decenoic acid;
  • PSA 57.53000
  • LogP 1.96010

Synthetic route

(E)-ethyl 10-acetoxydec-2-enoate
1338457-45-6

(E)-ethyl 10-acetoxydec-2-enoate

(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

Conditions
ConditionsYield
With water; sodium hydroxide In ethanol at 60℃; for 4h;99.2%
10-hydroxy-dec-2t-enoic acid methyl ester
68750-32-3

10-hydroxy-dec-2t-enoic acid methyl ester

(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

Conditions
ConditionsYield
With sodium hydroxide at 20℃; for 4h; Time;97%
10-hydroxy 8-decenoic acid ethyl ester
57221-93-9

10-hydroxy 8-decenoic acid ethyl ester

(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

Conditions
ConditionsYield
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

10-hydroxy-3-decenoic acid

(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

Conditions
ConditionsYield
With potassium hydroxide for 3h; Heating;65%
8-hydroxyoctanal
22054-14-4

8-hydroxyoctanal

malonic acid
141-82-2

malonic acid

(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

Conditions
ConditionsYield
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

malonic acid

acetic acid 8-oxo-octyl ester
40264-95-7

acetic acid 8-oxo-octyl ester

(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

Conditions
ConditionsYield
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

malonic acid

8,8-diethoxy-octan-1-ol
817-45-8

8,8-diethoxy-octan-1-ol

(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

Conditions
ConditionsYield
(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

malonic acid

Nonane-1,2,9-triol

Nonane-1,2,9-triol

(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

Conditions
ConditionsYield
(i) aq. KIO4, H2SO4, EtOH, (ii) /BRN= 1751370/, Py; Multistep reaction;
10-acetoxydecanoic acid
92038-37-4

10-acetoxydecanoic acid

(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

Conditions
ConditionsYield
(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

trans-10-Iod-2-decensaeure

(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

Conditions
ConditionsYield
(i) KOAc, AcOH, Py, (ii) KOH; Multistep reaction;
2-Brom-10-acetoxy-decansaeure-methylester
92157-89-6

2-Brom-10-acetoxy-decansaeure-methylester

(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

Conditions
ConditionsYield
(i) NaI, acetone, (ii) KOH, MeOH; Multistep reaction;
3,10-dihydroxydecanoic acid
762-05-0

3,10-dihydroxydecanoic acid

(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

Conditions
ConditionsYield
(i) Ac2O, (ii) KOH, EtOH; Multistep reaction;
Acetic acid 8,10,10,10-tetrachloro-decyl ester

Acetic acid 8,10,10,10-tetrachloro-decyl ester

(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

Conditions
ConditionsYield
(i) KOEt, (ii) aq. KOH; Multistep reaction;
8-chloro-1-octanal
72359-96-7

8-chloro-1-octanal

(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

Conditions
ConditionsYield
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

trans-10-Chlor-2-decensaeure

(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaI / acetone
2: (i) KOAc, AcOH, Py, (ii) KOH
View Scheme
2-bromo-9-chloro-nonanoyl chloride

2-bromo-9-chloro-nonanoyl chloride

(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

Conditions
ConditionsYield
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

8,8-diethoxy-octanoic acid ethyl ester

(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

Conditions
ConditionsYield
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)-8-Oxo-oct-2-enoic acid ethyl ester

(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

Conditions
ConditionsYield
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)-8,8-Diethoxy-oct-2-enoic acid ethyl ester

(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

Conditions
ConditionsYield
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

(2E,4E)-8,8-Diethoxy-octa-2,4-dienoic acid ethyl ester

(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

Conditions
ConditionsYield
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

1,9-diacetoxynon-1-ene

(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

Conditions
ConditionsYield
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

(Z)-Cyclooctene

hydrogen

hydrogen

(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

Conditions
ConditionsYield
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

8,8-dimethoxy-octan-1-ol

(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

Conditions
ConditionsYield
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

7-formylheptanoic acid

(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

Conditions
ConditionsYield
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

8,8-dimethoxyoctanoic acid methyl ester

(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

Conditions
ConditionsYield
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

7-Formyl-4Z-heptenoic acid

(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

Conditions
ConditionsYield
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

8-tetrahydropyranyloxyoctanal

(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

Conditions
ConditionsYield
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

ethyl (E)-10-(2-tetrahydropyranyloxy)-2-decenoate

(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

Conditions
ConditionsYield
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

oct-7-enal

(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

Conditions
ConditionsYield
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

(E)-10-hydroxy-dec-2-enoic acid

acetic anhydride
108-24-7

acetic anhydride

trans-10-acetoxydec-2-enoic acid
68750-29-8

trans-10-acetoxydec-2-enoic acid

Conditions
ConditionsYield
at 60 - 80℃; for 3h;97.6%
(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

propionic acid anhydride
123-62-6

propionic acid anhydride

(E)-10-propionyloxy-2-decenoic acid

(E)-10-propionyloxy-2-decenoic acid

Conditions
ConditionsYield
at 60 - 80℃; for 3h;96.1%
diazomethane
186581-53-3, 908094-01-9

diazomethane

(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

methyl 9-formyl-(E)-2-nonecate
81550-30-3

methyl 9-formyl-(E)-2-nonecate

Conditions
ConditionsYield
With pyridinium chlorochromate75%
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

1-{[(2E)-10-Hydroxydec-2-enoyl]oxy}pyrrolidine-2,5-dione

1-{[(2E)-10-Hydroxydec-2-enoyl]oxy}pyrrolidine-2,5-dione

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 5 - 20℃; for 24h;52%
(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

A

(2E,12E,22E)-triaconta-2,12,22-triene-1,11,21-triolide
128677-37-2

(2E,12E,22E)-triaconta-2,12,22-triene-1,11,21-triolide

B

(2E,12E)-eicosa-2,12-diene-1,11-diolide
83637-48-3

(2E,12E)-eicosa-2,12-diene-1,11-diolide

C

(3E,14E,25E,36E)-1,12,23,34-Tetraoxa-cyclotetratetraconta-3,14,25,36-tetraene-2,13,24,35-tetraone

(3E,14E,25E,36E)-1,12,23,34-Tetraoxa-cyclotetratetraconta-3,14,25,36-tetraene-2,13,24,35-tetraone

D

C50H80O10

C50H80O10

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In benzene at 20℃; for 72h;A n/a
B 24%
C n/a
D n/a
...Expand
diazomethane
186581-53-3, 908094-01-9

diazomethane

(E)-10-hydroxy-dec-2-enoic acid
14113-05-4

(E)-10-hydroxy-dec-2-enoic acid

10-hydroxy-dec-2t-enoic acid methyl ester
68750-32-3

10-hydroxy-dec-2t-enoic acid methyl ester

(E)-10-Hydroxy-2-decenoic acid Specification

The (E)-10-Hydroxy-2-decenoic acid, with the CAS registry number 14113-05-4,is also known as 10-Hydroxy-2-decenoic acid. It belongs to the product categories of intermediate.This chemical's molecular formula is C10H18O3 and molecular weight is 186.25. What's more,Its systematic name is 2-Decenoic acid,10-hydroxy-,(E)-.It is only used for laboratory content determination, pharmacological experiments, etc., shall not be used for medical diagnosis.

Physical properties about (E)-10-Hydroxy-2-decenoic acid are:
(1) ACD/LogP:  1.808; (2)# of Rule of 5 Violations:  0; (3)ACD/LogD (pH 5.5):  1.02; (4)ACD/LogD (pH 7.4):  -0.78; (5)ACD/BCF (pH 5.5):  2.25; (6)ACD/BCF (pH 7.4):  1.00; (7)ACD/KOC (pH 5.5):  36.97; (8)ACD/KOC (pH 7.4):  1.00; (9)#H bond acceptors:  3; (10)#H bond donors:  2; (11)#Freely Rotating Bonds:  9; (12)Index of Refraction:  1.486; (13)Molar Refractivity:  51.535 cm3; (14)Molar Volume:  179.349 cm3; (15)Surface Tension:  41.6920013427734 dyne/cm; (16)Density:  1.038 g/cm3; (17)Flash Point:  173.129 °C; (18)Enthalpy of Vaporization:  67.489 kJ/mol; (19)Boiling Point:  339.175 °C at 760 mmHg; (20)Vapour Pressure:  0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES:O=C(O)/C=C/CCCCCCCO;
(2)Std. InChI:InChI=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+;
(3)Std. InChIKey:QHBZHVUGQROELI-SOFGYWHQSA-N.

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