5,12-Dihydroxyicosa-6,8,10,14-tetraenoic acid

Base Information

• Chemical Name: 5,12-Dihydroxyicosa-6,8,10,14-tetraenoic acid
• CAS No.: 73151-67-4
• Molecular Formula: C₂₀H₃₂O₄
• Molecular Weight: 336.472
• DSSTox Substance ID: DTXSID40860923
• Wikidata: Q41596312
• Mol file: 73151-67-4.mol

Synonyms:5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid;73151-67-4;12-Epi leukotriene B4;LTB4;5(S),12(R)-DiHETE;starbld0003804;DTXSID40860923;FT-0604833;FT-0641355;FT-0641358;FT-0641916;FT-0643029;5,12-dihydroxyeicosa-6,8,10,14-tetraenoic acid;Q2704449;Q41596312

Chemical Property of 5,12-Dihydroxyicosa-6,8,10,14-tetraenoic acid

Chemical Property:

• Vapor Pressure: 9.63E-14mmHg at 25°C
• Refractive Index: 1.527
• Boiling Point: 536.4°C at 760 mmHg
• PKA: 4.68±0.10(Predicted)
• Flash Point: 292.3°C
• PSA: 77.76000
• Density: 1.04g/cm³
• LogP: 4.50750
• Storage Temp.: −20°C
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 14
• Exact Mass: 336.23005950
• Heavy Atom Count: 24
• Complexity: 421

Purity/Quality:

99%min ^*data from raw suppliers

5(S),12(S)-DiHETE ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36-7

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC(C=CC=CC=CC(CCCC(=O)O)O)O
• Uses: 5(S),12(S)-DiHETE is a compound that acts as a potent eicosanoid lipid mediator.

Technology Process of 5,12-Dihydroxyicosa-6,8,10,14-tetraenoic acid

There total 124 articles about 5,12-Dihydroxyicosa-6,8,10,14-tetraenoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

<5,6,8,9,11,12,14,15-3H8>arachidonic acid (66753-05-7) → Leukotriene B (71160-24-2) + 6-trans-Leukotriene B4 (70578-51-7,71160-24-2,71548-19-1,73151-67-4,77367-60-3,79056-01-2,79065-06-8,79083-59-3,79083-60-6,79897-16-8,82978-32-3,82978-33-4,83709-73-3,86161-62-8,86161-63-9,88643-26-9,90529-29-6,90638-64-5,101759-15-3,101759-16-4,108392-55-8,108392-56-9,117020-67-4,128946-47-4,128946-48-5,139560-82-0,71652-82-9) + 5(S)-HETE (61641-47-2,70608-72-9,71030-39-2,71774-09-9,72255-35-7,73307-52-5,74080-72-1,88588-79-8) + (5S,12S,6E,8Z,10E,14Z)-5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid (70578-51-7,71160-24-2,71548-19-1,71652-82-9,73151-67-4,77367-60-3,79065-06-8,79083-59-3,79083-60-6,79897-16-8,82978-32-3,82978-33-4,83709-73-3,86161-62-8,86161-63-9,88643-26-9,90529-29-6,90638-64-5,101759-15-3,101759-16-4,108392-55-8,108392-56-9,117020-67-4,128946-47-4,128946-48-5,139560-82-0,79056-01-2)

Guidance literature:

With ATP; calcium(II) nitrate; edetate disodium; In phosphate buffer; water; at 30 ℃; for 0.25h; pH=7.4; Further byproducts.;

DOI:10.1002/jlcr.1488

Reference yield:

<5,6,8,9,11,12,14,15-3H8>arachidonic acid (66753-05-7) → Leukotriene B (71160-24-2) + 6-trans-Leukotriene B4 (70578-51-7,71160-24-2,71548-19-1,73151-67-4,77367-60-3,79056-01-2,79065-06-8,79083-59-3,79083-60-6,79897-16-8,82978-32-3,82978-33-4,83709-73-3,86161-62-8,86161-63-9,88643-26-9,90529-29-6,90638-64-5,101759-15-3,101759-16-4,108392-55-8,108392-56-9,117020-67-4,128946-47-4,128946-48-5,139560-82-0,71652-82-9) + 5(S)-HETE (61641-47-2,70608-72-9,71030-39-2,71774-09-9,72255-35-7,73307-52-5,74080-72-1,88588-79-8) + (5S,12S,6E,8Z,10E,14Z)-5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid (70578-51-7,71160-24-2,71548-19-1,71652-82-9,73151-67-4,77367-60-3,79065-06-8,79083-59-3,79083-60-6,79897-16-8,82978-32-3,82978-33-4,83709-73-3,86161-62-8,86161-63-9,88643-26-9,90529-29-6,90638-64-5,101759-15-3,101759-16-4,108392-55-8,108392-56-9,117020-67-4,128946-47-4,128946-48-5,139560-82-0,79056-01-2)

Guidance literature:

With ATP; calcium(II) nitrate; edetate disodium; In phosphate buffer; water; at 30 ℃; for 0.25h; pH=7.4; Further byproducts.;

DOI:10.1002/jlcr.1488

Reference yield:

(E)-4-((4S,5R)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-2-enoic acid methyl ester (76745-14-7) → 6-trans-Leukotriene B4 (70578-51-7,71160-24-2,71548-19-1,73151-67-4,77367-60-3,79056-01-2,79065-06-8,79083-59-3,79083-60-6,79897-16-8,82978-32-3,82978-33-4,83709-73-3,86161-62-8,86161-63-9,88643-26-9,90529-29-6,90638-64-5,101759-15-3,101759-16-4,108392-55-8,108392-56-9,117020-67-4,128946-47-4,128946-48-5,139560-82-0,71652-82-9)

Guidance literature:

Multi-step reaction with 7 steps

1: hydrogen / 10percent palladium-on-charcoal / ethyl acetate / 4 h / 23 °C

2: pyridine / 12 h / 23 °C

3: 1.) 2percent methanolic HCl, 2.) potassium carbonate / 1.) 23 deg C, 7 h, 2.) methanol, 23 deg C, 30 min

4: pyridine / 1 h / 23 °C

5: 1.) 70percent perchloric acid, dimethyl carbonate, 2.) lead tetracetate, sodium carbonate / 1.) water, 23 deg C, 4 h, 2.) methylene chloride, -40 deg C, 10 min

6: 32 percent / n-butyllithium, HMPA / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) -78 deg C -> -20 deg C, 30 min, 3.) -20 deg C -> 0 deg C, 30 min

7: 1.) potassium carbonate, 2.) lithium hydroxide / 1.) methanol, 25 deg C, 6.5 h, 2.) methanol-water (2:1) 23 deg C, 1 h

With lead(IV) acetate; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hydroxide; n-butyllithium; perchloric acid; hydrogen; sodium carbonate; potassium carbonate; carbonic acid dimethyl ester; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethyl acetate;

DOI:10.1021/ja00547a051

upstream raw materials:

Leukotriene B

Benzoic acid (2E,4E)-(S)-1-(3-methoxycarbonyl-propyl)-6-oxo-hexa-2,4-dienyl ester

(7E,9E,11Z,14Z)-(5S,6R)-6-[(R)-2-((S)-4-Amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid

methyl 5(S)-(benzoyloxy)-12(R)-hydroxy-6(Z),8(E),10(E),14(Z)-eicosatetraenoate

Downstream raw materials:

(6E,8Z,10Z,14Z)-(5S,12S)-5,12-Dihydroxy-icosa-6,8,10,14-tetraenoic acid methyl ester

LTB_x methyl ester

(6E,8Z,10Z,14Z)-(5R,12S)-5,12-Dihydroxy-icosa-6,8,10,14-tetraenoic acid methyl ester

(6E,8Z,10E,14Z)-(5R,12S)-5,12-Dihydroxy-icosa-6,8,10,14-tetraenoic acid methyl ester

Refernces

• 1、 Schramm, Stanislav I.,Nagaev, Igor Yu.,Sabirsh, Alan,Shevchenko, Valeriy P.,Arkhipova, Anastasiya S.,Haeggstroem, Jesper Z.,Myasoedov, Nikolay F.. "Preparation of high specific activity tritium-labelled leukotriene B 4 suitable for radioligand binding assay". . p. 101 - 105. Retrieved 2008/09/20.
• 2、 Kobayashi, Yuichi,Shimazaki, Toshiyuki,Taguchi, Hideki,Sato, Fumie. "Highly Stereocontrolled Total Synthesis of Leukotriene B4, 20-Hydroxyleukotriene B4, Leukotriene B3, and Their Analogues". . p. 5324 - 5335. Retrieved 2007/10/02.