all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate
docosahexaenoic acid
Conditions | Yield |
---|---|
With ethylenediaminetetraacetic acid; edetate disodium In ethanol; water at 60 - 65℃; for 2h; | 98% |
With sodium hydroxide; edetate disodium In ethanol at 65℃; | 98% |
Stage #1: all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate With water; sodium hydroxide In methanol at 20℃; for 1.5h; Stage #2: With hydrogenchloride In methanol; water Cooling with ice; | 91% |
docosahexaenoic acid
Conditions | Yield |
---|---|
With lithium hydroxide monohydrate In ethanol; water at 60℃; for 1h; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
With lithium hydroxide In tetrahydrofuran; water | 92% |
Stage #1: all-cis-4,7,10,13,16,19-docosahexaenoic acid methyl ester With water; lithium hydroxide In tetrahydrofuran at 0 - 20℃; for 12h; Stage #2: With citric acid In water at 0℃; pH=~ 4; |
all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate
serinol
A
docosahexaenoic acid
Conditions | Yield |
---|---|
With Novozym 435 lipase on resin In acetone at 35℃; for 4h; Green chemistry; Enzymatic reaction; | A n/a B 87% |
3-Amino-1,2-propanediol
all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate
A
docosahexaenoic acid
B
(4Z,7Z,10Z,13Z,16Z,19Z)-N-(2,3-dihydroxypropyl)docosa-4,7,10,13,16,19-hexaenamide
Conditions | Yield |
---|---|
With Novozym 435 lipase on resin In acetone at 35℃; for 8h; Green chemistry; Enzymatic reaction; | A n/a B 80% |
all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate
ethanolamine
A
docosahexaenoic acid
B
N-docosahexaenoylethanolamine
Conditions | Yield |
---|---|
With Novozym 435 lipase on resin In acetone at 35℃; for 8h; Green chemistry; Enzymatic reaction; | A n/a B 75% |
(R)-2-aminopropan-1-ol
all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate
A
docosahexaenoic acid
B
(4Z,7Z,10Z,13Z,16Z,19Z)-N-((R)-1-hydroxypropan-2-yl)docosa-4,7,10,13,16,19-hexaenamide
Conditions | Yield |
---|---|
With Novozym 435 lipase on resin In acetone at 35℃; for 8h; Green chemistry; Enzymatic reaction; | A n/a B 70% |
all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate
(R)-3-amino-1,2-propanediol
A
docosahexaenoic acid
Conditions | Yield |
---|---|
With Novozym 435 lipase on resin In acetone at 35℃; for 8h; Green chemistry; Enzymatic reaction; | A n/a B 70% |
(S)-3-Amino-1,2-propanediol
all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate
A
docosahexaenoic acid
Conditions | Yield |
---|---|
With Novozym 435 lipase on resin In acetone at 35℃; for 8h; Green chemistry; Enzymatic reaction; | A n/a B 65% |
all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate
ethylenediamine
A
docosahexaenoic acid
B
(4Z,7Z,10Z,13Z, 16Z,19Z)docosa-4,7,10,13,16,19-hexaenoic acid [2-((4Z,7Z,10Z,13Z, 16Z,19Z)docosa-4,7,10,13,16,19-hexaenoylamino)ethyl]amide
Conditions | Yield |
---|---|
With Novozym 435 lipase on resin In acetone at 35℃; for 8h; Green chemistry; Enzymatic reaction; | A n/a B 60% |
serin
all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate
A
docosahexaenoic acid
Conditions | Yield |
---|---|
With Novozym 435 lipase on resin In acetone at 35℃; for 8h; Green chemistry; Enzymatic reaction; | A n/a B 55% |
all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate
1,3-Diamino-2-hydroxypropane
A
docosahexaenoic acid
Conditions | Yield |
---|---|
With Novozym 435 lipase on resin In acetone at 35℃; for 8h; Green chemistry; Enzymatic reaction; | A n/a B 48% C 38% |
docosahexaenoic acid
Conditions | Yield |
---|---|
With sodium thiosulfate In water Yield given; |
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: pyridine, Ph3PBr2 / acetonitrile / 0 °C 2: acetonitrile / 24 h / Heating 3: 56 percent / NaN(SiMe3)2 / tetrahydrofuran / 1.) room temperature, 2.) -90 deg C 4: 100 percent / H+ / tetrahydrofuran 5: 86 percent / LiAlH4 / tetrahydrofuran / -70 °C 6: 94 percent / CBr4, Ph3P / CH2Cl2 / 1.) 0 deg C, 15 min, 2.) room temperature, 1 h 7: 95 percent / acetonitrile / Heating 8: 76 percent / NaN(SiMe3)2 / tetrahydrofuran / -80 °C 9: 92 percent / LiOH / tetrahydrofuran; H2O View Scheme |
1-bromo-3-hexene
docosahexaenoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: acetonitrile / 24 h / Heating 2: 56 percent / NaN(SiMe3)2 / tetrahydrofuran / 1.) room temperature, 2.) -90 deg C 3: 100 percent / H+ / tetrahydrofuran 4: 86 percent / LiAlH4 / tetrahydrofuran / -70 °C 5: 94 percent / CBr4, Ph3P / CH2Cl2 / 1.) 0 deg C, 15 min, 2.) room temperature, 1 h 6: 95 percent / acetonitrile / Heating 7: 76 percent / NaN(SiMe3)2 / tetrahydrofuran / -80 °C 8: 92 percent / LiOH / tetrahydrofuran; H2O View Scheme |
(3Z,6Z,9Z)-dodecatrien-1-ol
docosahexaenoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 94 percent / CBr4, Ph3P / CH2Cl2 / 1.) 0 deg C, 15 min, 2.) room temperature, 1 h 2: 95 percent / acetonitrile / Heating 3: 76 percent / NaN(SiMe3)2 / tetrahydrofuran / -80 °C 4: 92 percent / LiOH / tetrahydrofuran; H2O View Scheme |
(3Z)-3-hexenyltriphenylphosphonium bromide
docosahexaenoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 56 percent / NaN(SiMe3)2 / tetrahydrofuran / 1.) room temperature, 2.) -90 deg C 2: 100 percent / H+ / tetrahydrofuran 3: 86 percent / LiAlH4 / tetrahydrofuran / -70 °C 4: 94 percent / CBr4, Ph3P / CH2Cl2 / 1.) 0 deg C, 15 min, 2.) room temperature, 1 h 5: 95 percent / acetonitrile / Heating 6: 76 percent / NaN(SiMe3)2 / tetrahydrofuran / -80 °C 7: 92 percent / LiOH / tetrahydrofuran; H2O View Scheme |
(Z)-6,6-diisopropoxyhex-3-en-1-al
docosahexaenoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 51 percent / NaN(SiMe3)2 / tetrahydrofuran / 1.) room temperature, 2.) -90 deg C 2: H+ / tetrahydrofuran 3: 76 percent / NaN(SiMe3)2 / tetrahydrofuran / -80 °C 4: 92 percent / LiOH / tetrahydrofuran; H2O View Scheme |
(Z,Z,Z)-1-bromododeca-3,6,9-triene
docosahexaenoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 95 percent / acetonitrile / Heating 2: 76 percent / NaN(SiMe3)2 / tetrahydrofuran / -80 °C 3: 92 percent / LiOH / tetrahydrofuran; H2O View Scheme |
(Z,Z,Z)-dodeca-3,6,9-trien-1-al
docosahexaenoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 86 percent / LiAlH4 / tetrahydrofuran / -70 °C 2: 94 percent / CBr4, Ph3P / CH2Cl2 / 1.) 0 deg C, 15 min, 2.) room temperature, 1 h 3: 95 percent / acetonitrile / Heating 4: 76 percent / NaN(SiMe3)2 / tetrahydrofuran / -80 °C 5: 92 percent / LiOH / tetrahydrofuran; H2O View Scheme |
(Z,Z)-10-oxodeca-4,7-dienoic acid methyl ester
docosahexaenoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 76 percent / NaN(SiMe3)2 / tetrahydrofuran / -80 °C 2: 92 percent / LiOH / tetrahydrofuran; H2O View Scheme |
(Z,Z,Z)-1,1-diisopropoxydodeca-3,6,9-triene
docosahexaenoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 100 percent / H+ / tetrahydrofuran 2: 86 percent / LiAlH4 / tetrahydrofuran / -70 °C 3: 94 percent / CBr4, Ph3P / CH2Cl2 / 1.) 0 deg C, 15 min, 2.) room temperature, 1 h 4: 95 percent / acetonitrile / Heating 5: 76 percent / NaN(SiMe3)2 / tetrahydrofuran / -80 °C 6: 92 percent / LiOH / tetrahydrofuran; H2O View Scheme |
(Z,Z)-10,10-diisopropoxydeca-4,7-dienoic acid methyl ester
docosahexaenoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: H+ / tetrahydrofuran 2: 76 percent / NaN(SiMe3)2 / tetrahydrofuran / -80 °C 3: 92 percent / LiOH / tetrahydrofuran; H2O View Scheme |
docosahexaenoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 76 percent / NaN(SiMe3)2 / tetrahydrofuran / -80 °C 2: 92 percent / LiOH / tetrahydrofuran; H2O View Scheme |
5-((3Z,6Z,9Z,12Z,15Z)-1-iodooctadeca-3,6,9,12,15-pentaenyl)dihydro-2(3H)-furanone
docosahexaenoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium iodide / acetonitrile / 1 h / 23 °C 2: sodium thiosulfate / H2O View Scheme |
all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate
eicosapentaenoic acid ethyl ester
A
all cis-5,8,11,14,17-eicosapentaenoic acid
B
docosahexaenoic acid
Conditions | Yield |
---|---|
Stage #1: all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate; eicosapentaenoic acid ethyl ester With water; sodium hydroxide In methanol at 20℃; for 1.5h; Stage #2: With hydrogenchloride In water Cooling with ice; |
Conditions | Yield |
---|---|
Stage #1: D-glucose; Labyrinthulae strain mh313 microorganism In water at 28℃; for 96h; pH=6.0; Enzymatic reaction; Stage #2: With hydrogenchloride; methanol Product distribution / selectivity; |
Conditions | Yield |
---|---|
With Nannochloropsis Gaditana Microbiological reaction; Photolysis; Large scale; |
all-(Z)-ethyl 4,7,10,13,16,19-docosahexaenoate
glycerol
A
docosahexaenoic acid
Conditions | Yield |
---|---|
With Novozyme 435 immobilized on polystyrene at 35℃; for 24h; Solvent; Green chemistry; Enzymatic reaction; |
diazomethane
docosahexaenoic acid
all-cis-4,7,10,13,16,19-docosahexaenoic acid methyl ester
Conditions | Yield |
---|---|
In diethyl ether | 100% |
docosahexaenoic acid
(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyl chloride
Conditions | Yield |
---|---|
With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 2h; | 100% |
With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h; Cooling with ice; | 100% |
With oxalyl dichloride In chloroform for 2h; |
docosahexaenoic acid
(±)-19,20-epoxy-4Z,7Z,10Z,13Z,16Z-docosapentaenoic acid
Conditions | Yield |
---|---|
With human recombinant cytochrome P450 1A1 Enzymatic reaction; stereoselective reaction; | 100% |
With MS-PPOH |
all cis-5,8,11,14,17-eicosapentaenoic acid
docosahexaenoic acid
Conditions | Yield |
---|---|
With Tocopherol In methanol; ethyl acetate at 50℃; for 0.333333h; Inert atmosphere; | 100% |
docosahexaenoic acid
1-t-Butoxycarbonylpiperazine
tert-butyl 4-(4Z,7Z,10Z,13Z,16Z, 19Z)-docosa-4,7,10,13,16,19-hexaenoylpiperazine-1-carboxylate
Conditions | Yield |
---|---|
With triethylamine; HATU In acetonitrile at 20℃; for 16h; | 99% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Steglich Esterification; | 99% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Steglich Esterification; | 99% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1 - 2h; | 98% |
With dmap; dacarbazine In dichloromethane at 20℃; |
Conditions | Yield |
---|---|
In methanol at 50℃; Inert atmosphere; | 98% |
docosahexaenoic acid
5-((3Z,6Z,9Z,12Z,15Z)-1-iodooctadeca-3,6,9,12,15-pentaenyl)dihydro-2(3H)-furanone
Conditions | Yield |
---|---|
With hydrogen iodide; iodine; potassium hydrogencarbonate In ethanol at 0 - 4℃; for 18h; Inert atmosphere; Darkness; | 97% |
With 2,6-dimethylpyridine; iodine In dichloromethane at 0℃; for 15h; Inert atmosphere; Cooling with ice; | 96% |
With iodine; potassium hydrogencarbonate; potassium iodide In tetrahydrofuran; water for 48h; Ambient temperature; | 95% |
Conditions | Yield |
---|---|
Stage #1: docosahexaenoic acid; glycine ethyl ester hydrochloride With dmap; triethylamine In dichloromethane at 20℃; for 0.0833333h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere; | 97% |
With benzotriazol-1-ol; 1,2-dichloro-ethane; triethylamine In dichloromethane at 20℃; for 18h; | 55% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 18h; | 55% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 18h; | 55% |
Conditions | Yield |
---|---|
With Tocopherol In ethanol; ethyl acetate at 60℃; | 97% |
Conditions | Yield |
---|---|
Stage #1: docosahexaenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Stage #2: ethanolamine In dichloromethane for 12h; | 96% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere; | 92% |
With Novozym 435, consisting of immobilized Candida antarctica lipase B In acetonitrile at 40℃; for 15h; Enzymatic reaction; | 20% |
docosahexaenoic acid
Conditions | Yield |
---|---|
With Tocopherol In methanol; ethyl acetate at 50℃; for 0.333333h; Inert atmosphere; | 96% |
docosahexaenoic acid
(4Z,7Z,10Z,13Z,16Z,19Z)-N-hydroxydocosa-4,7,10,13,16,19-hexaenamide
Conditions | Yield |
---|---|
Stage #1: docosahexaenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Stage #2: With hydroxylamine In dichloromethane for 12h; | 96% |
docosahexaenoic acid
Conditions | Yield |
---|---|
Stage #1: docosahexaenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Stage #2: With ammonia In dichloromethane for 12h; | 96% |
Conditions | Yield |
---|---|
Stage #1: docosahexaenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Stage #2: pyrrolidine In dichloromethane for 12h; | 96% |
Conditions | Yield |
---|---|
Stage #1: docosahexaenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Stage #2: piperidine In dichloromethane for 12h; | 96% |
Conditions | Yield |
---|---|
Stage #1: docosahexaenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Stage #2: morpholine In dichloromethane for 12h; | 96% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere; |
Conditions | Yield |
---|---|
Stage #1: docosahexaenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Stage #2: 1-methyl-piperazine In dichloromethane for 12h; | 96% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere; |
Conditions | Yield |
---|---|
Stage #1: docosahexaenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Stage #2: benzylamine In dichloromethane for 12h; | 96% |
Conditions | Yield |
---|---|
Stage #1: docosahexaenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Stage #2: rac-methylbenzylamine In dichloromethane for 12h; | 96% |
Conditions | Yield |
---|---|
Stage #1: docosahexaenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Stage #2: (R)-1-phenyl-ethyl-amine In dichloromethane for 12h; | 96% |
Conditions | Yield |
---|---|
Stage #1: docosahexaenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Stage #2: (S)-1-phenyl-ethylamine In dichloromethane for 12h; | 96% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 15h; | 95% |
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 80h; | 25% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h; |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 15h; | 95% |
Conditions | Yield |
---|---|
With triethylamine; carbonochloridic acid, butyl ester In tetrahydrofuran; methanol; acetonitrile at 20℃; for 2h; | 95% |
docosahexaenoic acid
(R)-1-O-octadecyl-3-decanoyl-sn-glycerol
(R)-1-O-octadecyl-2-docosahexaenoyl-3-decanoyl-sn-glycerol
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 15h; Inert atmosphere; | 95% |
The CAS registry number of Docosahexaenoic acid is 6217-54-5. The IUPAC name is (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid. In addition, the molecular formula is C22H32O2 and the molecular weight is 328.49. It is also called 4-cis,7-cis,10-cis,13-cis,16-cis,19-cis-docosahexaenoic acid. What's more, it is an omega-3 fatty acid and belongs to the classes of Biochemistry; Higher Fatty Acids & Higher Alcohols; Unsaturated Higher Fatty Acids; Fatty Acid Derivatives & Lipids; Glycerols. It should be stored in sealed container which filled with nitrogen, and put them in a cool and dry place
Physical properties about this chemical are: (1)ACD/LogP: 6.78; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.81; (4)ACD/LogD (pH 7.4): 4.01; (5)ACD/BCF (pH 5.5): 8976.76; (6)ACD/BCF (pH 7.4): 141.05; (7)ACD/KOC (pH 5.5): 12478.48; (8)ACD/KOC (pH 7.4): 196.07; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 14; (12)Polar Surface Area: 26.3 Å2; (13)Index of Refraction: 1.52; (14)Molar Refractivity: 105.88 cm3; (15)Molar Volume: 347.9 cm3; (16)Polarizability: 41.97 ×10-24cm3; (17)Surface Tension: 36 dyne/cm; (18)Density: 0.943 g/cm3; (19)Flash Point: 343.4 °C; (20)Enthalpy of Vaporization: 77.28 kJ/mol; (21)Boiling Point: 446.7 °C at 760 mmHg; (22)Vapour Pressure: 3.16E-09 mmHg at 25°C.
Preparation of Docosahexaenoic acid: it is commercially manufactured from microalgae; crypthecodinium cohnii and another of the genus schizochytrium. It is manufactured internally from α-linolenic acid, a shorter omega-3 fatty acid manufactured by plants (and also occurring in animal products as obtained from plants). Moreover, it can be prepared by cis-4,7,10,13,16,19-docosahexaneoic acid ethyl ester. This reaction will need reagents EDTA and Na2EDTA*2H2O, and solvents ethanol and H2O. The reaction time is 2 hours at reaction temperature of 60-65 °C. The yield is about 98%.
Uses of Docosahexaenoic acid: it can be used as a nutritional fortifiersit. And it can be used to treat hypertension, diabetes, menopausal syndrome, Parkinson's disease, asthma and eczema. Moreover, it is actively promoted by manufacturers as a food additive. In addition, it can react with diazomethane to get docosa-4c,7c,10c,13c,16c,19c-hexaenoic acid methyl ester. This reaction will need solvent diethyl ether. The yield is about 100%.
When you are using this chemical, please be cautious about it as the following:
During using it, you should avoid contact with skin and eyes. And do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer).
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)CC/C=C/C/C=C/C\C=C/C/C=C/C/C=C/C/C=C/CC
(2)InChI: InChI=1/C22H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h3-4,6-7,9-10,12-13,15-16,18-19H,2,5,8,11,14,17,20-21H2,1H3,(H,23,24)/b4-3+,7-6+,10-9+,13-12-,16-15+,19-18+
(3)InChIKey: MBMBGCFOFBJSGT-CHRIZAQABI
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