8,10-DODECADIEN-1-OL CAS#: 33956-49-9

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

Product Name8,10-DODECADIEN-1-OL
IUPAC Name(8E,10E)-dodeca-8,10-dien-1-ol
Molecular StructureStructure of 8E, 10E-dodecadien-1-ol CAS 33956-49-9
CAS Registry Number 33956-49-9
Synonyms(8E,10E)-dodeca-8,10-dienol;CAS Number: 33956-49-9; CAS NO:.33956-49-9
Molecular FormulaC12H22O
Molecular Weight182.30
InChIInChI=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+
InChI KeyCSWBSLXBXRFNST-MQQKCMAXSA-N
Canonical SMILESC/C=C/C=C/CCCCCCCO
Patent Information
Patent IDTitlePublication Date
US2010/113837Production of pheromones and fragrances from substituted and unsubstituted 1-alken-3yl alkylates2010
US2006/88563Use of spray adjuvant to enhance the movement of pesticides through plant canopies to the target2006
US6838576Process for preparing functional group-containing olefinic compounds2005

Physical Data

AppearanceColorless or light yellow crystalline
Refractive index1.5050 (estimate)
Melting Point, °C Solvent (Melting Point)
29 – 30
27 – 28.5
31 – 32pentane
28 – 29petroleum ether
Boiling Point, °CPressure (Boiling Point), Torr
98 – 1010.5
90 – 920.001
120 – 1220.5
120 – 1211
1220.5
1050.1
80 – 900.01

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)
Spectrum13C
Spectrum1H
Chemical shifts1HCDCl3
Chemical shifts13CCDCl3
Chemical shifts1HCCl4
Chemical shifts1Hbenzene-d6
Chemical shifts13Cbenzene-d6
Spin-spin coupling constantsCDCl3
Spin-spin coupling constantsbenzene-d6
8,10-DODECADIEN-1-OL CAS#: 33956-49-9 HNMRHNMR of 8E, 10E-dodecadien-1-ol CAS 33956-49-9
8,10-DODECADIEN-1-OL CAS#: 33956-49-9 CNMRCNMR of 8E, 10E-dodecadien-1-ol CAS 33956-49-9
Description (IR Spectroscopy)Solvent (IR Spectroscopy)Comment (IR Spectroscopy)
Bandsneat (no solvent)3320 – 920 cm**(-1)
BandsCHCl32930 – 990 cm**(-1)
Bandsneat (no solvent)3350 – 990 cm**(-1)
BandsKBr3350 cm**(-1)
Bands3340 – 985 cm**(-1)
IR
Description (Mass Spectrometry)
spectrum
spectrum, electron impact (EI)
spectrum, chemical ionization (CI)
fragmentation pattern, spectrum
electron impact (EI), spectrum
Description (UV/VIS Spectroscopy)Solvent (UV/VIS Spectroscopy)Comment (UV/VIS Spectroscopy)Absorption Maxima (UV/VIS), nmExt./Abs. Coefficient, l·mol-1cm-1
Spectrum205 – 300 nm
Absorption maximaaq. ethanol229.928000
Absorption maximahexane22922800
UV/VIS

Route of Synthesis (ROS)

Route of Synthesis (ROS) of 8,10-DODECADIEN-1-OL CAS# 33956-49-9
Route of Synthesis (ROS) of 8,10-DODECADIEN-1-OL CAS# 33956-49-9
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;

Experimental Procedure
1.C; 2.C Target product synthesis Example 1: E8, E10-dodecadien-1-ol
In a 1500L dry clean enamel reactor, enter 400kg of metered toluene, replace with nitrogen, put 46kg of chopped clean metal sodium, heat up to 80 ° C, cool under stirring, cool with ice water, cool to 10 ° C, drop by A mixture of intermediate B137 kg and intermediate C208.5 kg.Control 0-10 ° C drop, add dropwise, warm to 60 ° C, heat preservation reaction for 12 hours,Cool to 0 ° C, add 300 kg of water, 98 kg of sulfuric acid, control hydrolysis temperature 20 ° C, hydrolysis and stirring for 1 hour, check the water layer pH 3-4, layering, 200 kg of organic layer washed once, separate the water layer, organic layer negative pressure Concentrated to the solvent without, the remaining liquid enters the rectification column rectification, collecting 10mmHg, 118-120 ° C fraction, as shown in Figure 1,Detecting the E, E-isomer content of 99.5%,The quantity is: 141kg. The yield was 77.47%.The total yield was: 68%.
77.47%

Safety and Hazards

Pictogram(s)exclamation-markhealth-hazardenvironment
SignalDanger
GHS Hazard StatementsH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
H317 (64.62%): May cause an allergic skin reaction [Warning Sensitization, Skin]
H334 (29.23%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]
H400 (99.23%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
H410 (63.85%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]
Information may vary between notifications depending on impurities, additives, and other factors.
Precautionary Statement CodesP261, P264, P272, P273, P280, P285, P302+P352, P304+P341, P321, P332+P313, P333+P313, P342+P311, P362, P363, P391, and P501
(The corresponding statement to each P-code can be found at the GHS Classification page.)

Other Data

TransportationClass 8; Packaging Group: III; UN Number: 3082
Under the room temperature and away from light
StorageUnder the room temperature and away from light
Market PriceUSD
Druglikeness
Lipinski rules component
Molecular Weight182.306
logP4.548
HBA1
HBD1
Matching Lipinski Rules4
Veber rules component
Polar Surface Area (PSA)20.23
Rotatable Bond (RotB)8
Matching Veber Rules2
Bioactivity
In vitro: Efficacy
Quantitative Results
Quantitative Results
1 of 10Biological materialcat
SV-CISM-2 cell line
Assay DescriptionIncrease in cGMP formation in SV-CISM-2 cells relative to control upon treatment with the compound at 10e-4M
ResultsActivity not calculated
MeasurementActivity
2 of 10 TargetMultidrug resistance protein 1:Wild
Substance action on targetInhibitor
Assay DescriptionInhibitory activity against P-glycoprotein mediated compound efflux was determined
3 of 10Biological materialcat
SV-CISM-2 cell line
Assay DescriptionFormation of cGMP in SV-CISM-2 cells upon treatment with the compound at 10e-4M
ResultsActivity not calculated
MeasurementActivity
4 of 10Biological materialcat
SV-CISM-2 cell line
Assay DescriptionFormation of cGMP in SV-CISM-2 cells upon treatment with the compound at 10e-6M
ResultsActivity not calculated
MeasurementActivity
5 of 10 Biological materialcat
SV-CISM-2 cell line
Assay DescriptionIncrease in cGMP formation in SV-CISM-2 cells relative to control upon treatment with the compound at 10e-8M
ResultsActivity not calculated
MeasurementActivity
6 of 10Biological materialcat
SV-CISM-2 cell line
Assay DescriptionIncrease in cGMP formation in SV-CISM-2 cells relative to control upon treatment with the compound at 10e-6M
ResultsActivity not calculated
MeasurementActivity
7 of 10Biological materialcat
SV-CISM-2 cell line
Assay DescriptionFormation of cGMP in SV-CISM-2 cells upon treatment with the compound at 10e-8M
ResultsActivity not calculated
MeasurementActivity
8 of 10EffectBehavioural Symptoms
Assay DescriptionTarget : Ascogaster quadridentata
Bioassay : bioassays conducted between hrs 2 and 12 of insects’ photophase (16:8 h light:dark cycle); parasitoids reaching filter paper contain. title comp. within 15 min classed as responders in vivo; vertical Y-shaped Pyrex glass olfactometers; 25-27 deg C; relat. humid. 50-70 percent; fluorescent “daylight”+wide-spectrum grow light; air drawn through apparatus; responses of walking of flying insects to odor sources record.
9 of 10Biological materialCydia pomonella
Assay DescriptionEffect : pheromone activity
Bioassay : dispensers: a piece of cotton dental roll (0.3-300 ng) and gray elastomer septa (0.1-30.0 μg); effect: upwind flights culminating in contact with the dispenser flight tunnel bioassay; males for bioassays were used three days after eclosion and 0.25-2.5 hr after darkening the room; flight tunnel: 210 cm in length, air speed 12 cm/sec, 23 deg C, dimly lighted overhead by red lights controlled by a rheostat
Resultsresponse: gray elastomer septa: ca. 10 to ca. 85 percent, cotton dental roll: 0 to ca. 70 percent
10 of 10Biological materialCydia pomonella
Assay DescriptionEffect : pheromone activity
Bioassay : effect: the number of males making a circling motion while wing fanning wing-flutter bioassay; pint fruit jar; males for bioassays were used 3 days after eclosion and 0.25-2.5 hr after darkening the room; the test room was dimly lighted by red lights; 3-mm-diameter glass rod with title comp. was inserted into the jar
Resultsresponse: 20.5-96.5 percent
Use Pattern
General chemicals
guest material for slow-release pheromon composition comprising mesoporous molecular sieve as host material
Chemical processes/laboratory use
synthesizing a sex pheromone of the codling moth
Agricultural use
method of controlling chestnut tortrix (Cydia splendana)
composition for controlling undesired insect infestation
Insect attractant

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