Product Name

  • Name

    8,10-DODECADIEN-1-OL

  • EINECS 251-761-2
  • CAS No. 33956-49-9
  • Article Data37
  • CAS DataBase
  • Density 0.862g/cm3
  • Solubility
  • Melting Point 30-32 °C
  • Formula C12H22 O
  • Boiling Point 270.7°Cat760mmHg
  • Molecular Weight 182.306
  • Flash Point 100.9°C
  • Transport Information
  • Appearance
  • Safety Moderately toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating vapors.
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 33956-49-9 (8,10-DODECADIEN-1-OL)
  • Hazard Symbols
  • Synonyms 8,10-Dodecadien-1-ol,(E,E)- (8CI);(8E,10E)-8,10-Dodecadien-1-ol;(8E,10E)-Dodecadien-1-ol;(E,E)-8,10-Dodecadien-1-ol;(E,E)-8,10-Dodecadien-l-ol;(E,E)-8,10-Dodecadienol;8-trans,10-trans-Dodecadien-1-ol;CP-MK;Codlelure;Codlemone;Feroflon SR 2;Feroflor SR 2;trans-8,trans-10-Dodecadien-1-ol;trans-trans-8,10-Dodecadien-1-ol;
  • PSA 20.23000
  • LogP 3.45160

Synthetic route

trans-2-methyl-5-(7-hydroxyheptyl)-3-sulfolene
87241-02-9

trans-2-methyl-5-(7-hydroxyheptyl)-3-sulfolene

(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

Conditions
ConditionsYield
With potassium carbonate In ethanol at 125℃; for 0.5h;100%
With potassium carbonate In ethanol at 125℃;98%
(E,E)-sorbyl acetate
57006-69-6

(E,E)-sorbyl acetate

trimethylsilyl 6-chloro-1-hexyl ether
34714-00-6

trimethylsilyl 6-chloro-1-hexyl ether

(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

Conditions
ConditionsYield
Stage #1: (E,E)-sorbyl acetate; trimethylsilyl 6-chloro-1-hexyl ether With sodium In toluene at 0 - 80℃; for 12h; Inert atmosphere; Green chemistry;
Stage #2: With sulfuric acid In water; toluene at 0 - 20℃; for 1h; Temperature; Green chemistry;		77.47%
(E)-9-(phenylsulfinyl)-10-dodecen-1-ol
83248-82-2

(E)-9-(phenylsulfinyl)-10-dodecen-1-ol

(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

Conditions
ConditionsYield
With triethylamine In toluene at 80℃; for 18h;60%
(8E,10Z)-dodeca-8,10-dien-1-ol
33956-50-2

(8E,10Z)-dodeca-8,10-dien-1-ol

(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

Conditions
ConditionsYield
With thiophenol at 100℃; for 2h;30%
dodec-8-en-10-yn-1-ol
39616-28-9, 113982-52-8

dodec-8-en-10-yn-1-ol

(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran; diethylene glycol dimethyl ether at 140℃; for 2h;10%
1,6-hexanediol
629-11-8

1,6-hexanediol

(E,E)-sorbyl acetate
57006-69-6

(E,E)-sorbyl acetate

(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

Conditions
ConditionsYield
Multistep reaction;
trans-Crotonaldehyde
123-73-9

trans-Crotonaldehyde

8-hydroxy-octyl-triphenyl-phosphonium bromide
65734-62-5

8-hydroxy-octyl-triphenyl-phosphonium bromide

(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

Conditions
ConditionsYield
With phenyllithium 1.) THF/diethyl ether, 20 min, 2.) -75 deg C, 15 min, -30 deg C, 30 min, 25 deg C; Yield given. Multistep reaction. Yields of byproduct given;
(8E,10E)-8,10-Dodecadienyl-(tetrahydro-2-pyranyl)ether
37935-49-2

(8E,10E)-8,10-Dodecadienyl-(tetrahydro-2-pyranyl)ether

(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol; water at 60℃; for 2h; Yield given;
With toluene-4-sulfonic acid In methanol at 50℃; for 2h; Yield given;
With methanesulfonic acid; water In methanol at 60℃; for 3h; Hydrolysis;0.74 g
With toluene-4-sulfonic acid In methanol at 70℃; for 0.5h;
(E,E)-sorbyl acetate
57006-69-6

(E,E)-sorbyl acetate

(6-((tetrahydro-2H-pyran-2-yl)oxy)hexyl)magnesium chloride
69049-76-9

(6-((tetrahydro-2H-pyran-2-yl)oxy)hexyl)magnesium chloride

(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

Conditions
ConditionsYield
With hydrogen cation; copper(l) iodide Yield given. Multistep reaction;
1-bromo-3E,5E-heptadiene
37935-45-8

1-bromo-3E,5E-heptadiene

C8H19ClMgOSi

C8H19ClMgOSi

(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

Conditions
ConditionsYield
With dilithium tetrachlorocuprate; water 1) -5 - 0 deg C, 3 h; 2) 20 deg C, 12 h, THF, ether; 2) aq. EtOH, 2 h, boiling; Yield given. Multistep reaction;
7-((1R,2S,3R,5S,6R,7S)-5-Methyl-4,4-dioxo-4λ6-thia-tricyclo[5.2.1.02,6]dec-8-en-3-yl)-heptan-1-ol
86593-91-1

7-((1R,2S,3R,5S,6R,7S)-5-Methyl-4,4-dioxo-4λ6-thia-tricyclo[5.2.1.02,6]dec-8-en-3-yl)-heptan-1-ol

(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

Conditions
ConditionsYield
at 600℃;
12-THPO-dodeca-2E,4-diene
37935-49-2, 74502-07-1, 75787-30-3, 96754-38-0, 96754-39-1

12-THPO-dodeca-2E,4-diene

A

(8Z,10E)-8,10-Dodecadien-1-ol
33956-50-2

(8Z,10E)-8,10-Dodecadien-1-ol

B

(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

Conditions
ConditionsYield
With methanol; toluene-4-sulfonic acid In water at 60℃;
With methanol; toluene-4-sulfonic acid In diethyl ether; water for 2h; Heating; Yield given. Yields of byproduct given;
(E)-8-Benzenesulfonyl-dodec-10-en-1-ol
107735-59-1

(E)-8-Benzenesulfonyl-dodec-10-en-1-ol

A

(8E,10Z)-dodeca-8,10-dien-1-ol
33956-50-2

(8E,10Z)-dodeca-8,10-dien-1-ol

B

(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at 60℃; for 1h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
8-Acetoxy-9-phenylsulphinyl-1-tetrahydropyranyloxydodec-10(E)-ene
96249-88-6

8-Acetoxy-9-phenylsulphinyl-1-tetrahydropyranyloxydodec-10(E)-ene

(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

Conditions
ConditionsYield
With sodium amalgam; pyridinium p-toluenesulfonate 1) MeOH, EtOAc, -35 deg C, 5 h, 2) MeOH, reflux, 3 h; Yield given. Multistep reaction;
(8E,10E)-1,8,10-Dodecatrien
69775-54-8

(8E,10E)-1,8,10-Dodecatrien

(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

Conditions
ConditionsYield
With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide 1) THF; 2) water.; Yield given. Multistep reaction;
(8E,10E)-8,10-Dodecadiensaeure-methylester
60099-82-3

(8E,10E)-8,10-Dodecadiensaeure-methylester

(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether 1.) r.t., 1 h, 2.) reflux, 1 h; Yield given;
2-[((8E,10E)-Dodeca-8,10-dienyl)oxy]-tetrahydro-pyran

2-[((8E,10E)-Dodeca-8,10-dienyl)oxy]-tetrahydro-pyran

A

(8E,10Z)-dodeca-8,10-dien-1-ol
33956-50-2

(8E,10Z)-dodeca-8,10-dien-1-ol

B

(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

(8E,10E)-8,10-dodecadien-1-oxytrimethylsilane
38568-98-8

(8E,10E)-8,10-dodecadien-1-oxytrimethylsilane

(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

Conditions
ConditionsYield
With water In ethanol for 2h; Heating;
With toluene-4-sulfonic acid In methanol; water at 60℃; for 3h; Temperature;117 g
ethyl 6-(chloroformyl)hexanoate
14794-32-2

ethyl 6-(chloroformyl)hexanoate

tricarbonyl(1,3-pentadiene)iron

tricarbonyl(1,3-pentadiene)iron

A

(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

B

(8E,10E)-dodeca-8,10-dienal
69775-58-2

(8E,10E)-dodeca-8,10-dienal

C

(E,E)-8,10-dodecadienoic acid

(E,E)-8,10-dodecadienoic acid

Conditions
ConditionsYield
Multistep reaction;
...Expand
methyl 2Z,5E-heptadienoate
40415-88-1

methyl 2Z,5E-heptadienoate

(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 98 percent / triethylamine / 12 h / 20 °C
2: 88 percent / LiAlH4 / diethyl ether / 3 h / 20 °C
3: 70 percent / PBr3, pyridine / hexane / 1) 0 deg C, 3h; 2) 20 deg C, 12 h
4: 1) Li2CuCl4; 2) water / 1) -5 - 0 deg C, 3 h; 2) 20 deg C, 12 h, THF, ether; 2) aq. EtOH, 2 h, boiling
View Scheme
(3E, 5E)-hepta-3,5-dien-1-ol
37944-01-7

(3E, 5E)-hepta-3,5-dien-1-ol

(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70 percent / PBr3, pyridine / hexane / 1) 0 deg C, 3h; 2) 20 deg C, 12 h
2: 1) Li2CuCl4; 2) water / 1) -5 - 0 deg C, 3 h; 2) 20 deg C, 12 h, THF, ether; 2) aq. EtOH, 2 h, boiling
View Scheme
methyl (3E,5Z)-3,5-heptadienoate
32793-94-5

methyl (3E,5Z)-3,5-heptadienoate

(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 81 percent / LiAlH4 / diethyl ether / 3 h / 20 °C
2: 70 percent / PBr3, pyridine / hexane / 1) 0 deg C, 2 h; 2) 20 deg C, 12 h
3: 1) Li2CuCl4; 2) p-toluenesulfonic acid / 1) THF, 0 deg C, 3 h, then 20 deg C, 12 h; 2) methanol, water, 60 deg C, 3 h
4: 30 percent / C6H5SH / 2 h / 100 °C
View Scheme
methyl (3E,5E)-3,5-heptadienoate
32775-96-5

methyl (3E,5E)-3,5-heptadienoate

(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 88 percent / LiAlH4 / diethyl ether / 3 h / 20 °C
2: 70 percent / PBr3, pyridine / hexane / 1) 0 deg C, 3h; 2) 20 deg C, 12 h
3: 1) Li2CuCl4; 2) water / 1) -5 - 0 deg C, 3 h; 2) 20 deg C, 12 h, THF, ether; 2) aq. EtOH, 2 h, boiling
View Scheme
(3E, 5Z)-hepta-3,5-dien-1-ol
85110-94-7

(3E, 5Z)-hepta-3,5-dien-1-ol

(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 70 percent / PBr3, pyridine / hexane / 1) 0 deg C, 2 h; 2) 20 deg C, 12 h
2: 1) Li2CuCl4; 2) p-toluenesulfonic acid / 1) THF, 0 deg C, 3 h, then 20 deg C, 12 h; 2) methanol, water, 60 deg C, 3 h
3: 30 percent / C6H5SH / 2 h / 100 °C
View Scheme
1-bromo-3E,5Z-heptadiene
85134-50-5

1-bromo-3E,5Z-heptadiene

(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1) Li2CuCl4; 2) p-toluenesulfonic acid / 1) THF, 0 deg C, 3 h, then 20 deg C, 12 h; 2) methanol, water, 60 deg C, 3 h
2: 30 percent / C6H5SH / 2 h / 100 °C
View Scheme
methyl 2,5Z-heptadienoate
18261-30-8, 32793-92-3, 32793-93-4, 40415-88-1, 41792-07-8

methyl 2,5Z-heptadienoate

(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: triethylamine / heptane / 12 h / Heating
2: 81 percent / LiAlH4 / diethyl ether / 3 h / 20 °C
3: 70 percent / PBr3, pyridine / hexane / 1) 0 deg C, 2 h; 2) 20 deg C, 12 h
4: 1) Li2CuCl4; 2) p-toluenesulfonic acid / 1) THF, 0 deg C, 3 h, then 20 deg C, 12 h; 2) methanol, water, 60 deg C, 3 h
5: 30 percent / C6H5SH / 2 h / 100 °C
View Scheme
4-propenyl-1,3-dioxane, E-isomer
114988-54-4

4-propenyl-1,3-dioxane, E-isomer

(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 76 percent / H2SO4 / 15 h / 20 - 60 °C
2: 33 percent / H2SO4 / 160 °C / 40 Torr
3: Li2CuCl4 / tetrahydrofuran / 3 h / -10 °C
4: 0.74 g / water; MsOH / methanol / 3 h / 60 °C
View Scheme
(E,E)-sorbyl acetate
57006-69-6

(E,E)-sorbyl acetate

Br-Mg-CH2-CH2-CH(OR)2

Br-Mg-CH2-CH2-CH(OR)2

(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Li2CuCl4 / tetrahydrofuran / 3 h / -10 °C
2: 0.74 g / water; MsOH / methanol / 3 h / 60 °C
View Scheme
(6-((tetrahydro-2H-pyran-2-yl)oxy)hexyl)magnesium chloride
69049-76-9

(6-((tetrahydro-2H-pyran-2-yl)oxy)hexyl)magnesium chloride

(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Li2CuCl4 / tetrahydrofuran / 3 h / -10 °C
2: 0.74 g / water; MsOH / methanol / 3 h / 60 °C
View Scheme
(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

Methanesulfonic acid (8E,10E)-dodeca-8,10-dienyl ester
88076-03-3

Methanesulfonic acid (8E,10E)-dodeca-8,10-dienyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane99%
(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

(8E,10E)-dodeca-8,10-dienal
69775-58-2

(8E,10E)-dodeca-8,10-dienal

Conditions
ConditionsYield
With pyridinium chlorochromate In dichloromethane65%
With pyridinium chlorochromate In dichloromethane at 20℃; for 2h;64%
With pyridinium chlorochromate In dichloromethane60%
(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

acetic anhydride
108-24-7

acetic anhydride

(E,E)-8,10-dodecadienyl acetate
53880-51-6

(E,E)-8,10-dodecadienyl acetate

(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

acetobromomaltose
61651-22-7, 76843-44-2, 141243-53-0

acetobromomaltose

8(E),10(E)-Dodecadienyl β-D-Maltopyranoside
86217-86-9

8(E),10(E)-Dodecadienyl β-D-Maltopyranoside

Conditions
ConditionsYield
Yield given. Multistep reaction;
(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

Sodium 8(E),10(E)-Dodecadienyl Sulfate
86217-85-8

Sodium 8(E),10(E)-Dodecadienyl Sulfate

Conditions
ConditionsYield
With sodium hydroxide; sulfur trioxide pyridine complex 1.) pyridine, 10 min.; Yield given. Multistep reaction;
(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

acetic anhydride
108-24-7

acetic anhydride

A

(8Z,10E)-8,10-dodecadienyl acetate
67992-59-0

(8Z,10E)-8,10-dodecadienyl acetate

B

(8E,10Z)-dodeca-8,10-dien-1-yl acetate
67992-60-3

(8E,10Z)-dodeca-8,10-dien-1-yl acetate

C

(E,E)-8,10-dodecadienyl acetate
53880-51-6

(E,E)-8,10-dodecadienyl acetate

Conditions
ConditionsYield
With pyridine Title compound not separated from byproducts;A 1.0 % Chromat.
B 4.0 % Chromat.
C 95.0 % Chromat.
...Expand
(8E,10E)-dodeca-8,10-dienol
33956-49-9

(8E,10E)-dodeca-8,10-dienol

2-hydroxy-2-methylpropanenitrile
75-86-5

2-hydroxy-2-methylpropanenitrile

(E,E)-trideca-9,11-dienenitrile

(E,E)-trideca-9,11-dienenitrile

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate 1.) ether, -20 deg C, 20 min, 2.) ether, -20 deg C, 20 h; Yield given. Multistep reaction;

8,10-Dodecadien-1-ol Consensus Reports

Reported in EPA TSCA Inventory.

8,10-Dodecadien-1-ol Specification

8,10-Dodecadien-1-ol, with the CAS NO.33956-49-9, is also called (e,e)-10-dodecadien-1-ol; 8e,10e-dodecadien-1-ol; ai3-34872; checkmatecm; codlelure; codlingmothpheromone; ent34872; pheroconcm. It has the Molecular Formula of C12H22O and the Molecular Weight of 182.3025. It is an exemption from the requirement of a tolerance.

Physical properties about 8,10-Dodecadien-1-ol are: (1)ACD/LogP: 4.096; (2)ACD/LogD (pH 5.5): 4.10; (3)ACD/LogD (pH 7.4): 4.10; (4)ACD/BCF (pH 5.5): 763.50; (5)ACD/BCF (pH 7.4): 763.50; (6)ACD/KOC (pH 5.5): 4028.25; (7)ACD/KOC (pH 7.4): 4028.25; (8)#H bond acceptors: 1; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 9; (11)Index of Refraction: 1.473; (12)Molar Refractivity: 59.294 cm3; (13)Molar Volume: 211.352 cm3 ; (14)Polarizability: 23.506 10-24cm3; (15)Surface Tension: 31.503999710083 dyne/cm; (16)Density: 0.863 g/cm3; (17)Flash Point: 100.936 °C; (18)Enthalpy of Vaporization: 59.084 kJ/mol; (19)Boiling Point: 270.679 °C at 760 mmHg; (20)Vapour Pressure: 0.00100000004749745 mmHg at 25°C

You can still convert the following datas into molecular structure:
(1)InChI=1S/C12H22O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h2-5,13H,6-12H2,1H3/b3-2+,5-4+;
(2)InChIKey=CSWBSLXBXRFNST-MQQKCMAXSA-N;
(3)SmilesOCCCCCCC\C=C\C=C\C;

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 oral > 3200mg/kg (3200mg/kg)   Special Publication of the Entomological Society of America. Vol. 78-1, Pg. 49, 1978.

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