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H1385

Sigma-Aldrich

n-Heptadecanoyl coenzyme A lithium salt

≥90%

Synonyme(s) :

[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-[[[[4-[[3-(2-heptadecanoylsulfanylethylamino)-3-oxopropyl]amino]-3-hydroxy-2,2-dimethyl-4-oxobutoxy]-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxymethyl]-4-hydroxyoxolan-3-yl] hydrogen phosp

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About This Item

Formule empirique (notation de Hill):
C38H68N7O17P3S
Numéro CAS:
3546-17-6
Poids moléculaire :
1019.97
Numéro MDL:
MFCD00079338
Code UNSPSC :
41106305
ID de substance PubChem :
24895454
Nomenclature NACRES :
NA.51

Pureté

≥90%

Température de stockage

−20°C

Chaîne SMILES 

CCCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)n2cnc3c(N)ncnc23

InChI

1S/C38H68N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-29(47)66-22-21-40-28(46)19-20-41-36(50)33(49)38(2,3)24-59-65(56,57)62-64(54,55)58-23-27-32(61-63(51,52)53)31(48)37(60-27)45-26-44-30-34(39)42-25-43-35(30)45/h25-27,31-33,37,48-49H,4-24H2,1-3H3,(H,40,46)(H,41,50)(H,54,55)(H,56,57)(H2,39,42,43)(H2,51,52,53)/t27-,31-,32-,33?,37-/m1/s1

Clé InChI

DRABUZIHHACUPI-UVICFMDKSA-N

Catégories apparentées

Actions biochimiques/physiologiques

Coenzyme A functions as an acyl group carrier, acetyl-CoA. Heptadecanoyl Coenzyme A (C17-CoA), a long-chain (C-17) saturated fatty acyl-CoA, is used as an intermediate in lipid metabolism. It is a substrate of acyl-CoA dehydrogenase (EC 1.3.99.3) within the mitochondria and of carnitine O-palmitoyltransferase (EC 2.3.1.21) within the cytoplasm. Heptadecanoyl Coenzyme A is an inhibitor of general acyl-coenzyme A dehydrogenase (EC 1.3.99.3).

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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M J Mangino et al.
Journal of chromatography, 577(1), 157-162 (1992-05-20)
A method has been developed that permits rapid and easy tissue extraction of long-chain acyl-coenzyme A (acyl-CoA) thioesters with sensitive quantitation by reversed-phase high-performance liquid chromatography (RP-HPLC). Tissue homogenants are extracted using a reserve Bligh-Dyer technique, and long-chain acyl-CoA esters
C Thorpe et al.
European journal of biochemistry, 118(2), 279-282 (1981-08-01)
The interaction of two long-chain acyl-CoA analogs with pig kidney general acyl-CoA dehydrogenase (EC 1.3.99,3) was examined. The effect of S-heptadecyl-CoA and heptadecan-2-onyl-dethio-CoA on the flavo-protein was observed spectrophotometrically using the flavin as an active-site probe. The S-heptadecyl thioether analog
Z Y Jiang et al.
The Biochemical journal, 207(3), 415-419 (1982-12-01)
The flavoenzyme pig kidney general acyl-CoA dehydrogenase (EC 1.3.99.3) is inactivated by cyclohexane-1,2-dione in borate buffer in a reaction that exhibits pseudo-first-order kinetics. Strong protection is afforded by the substrate octanoyl-CoA, as well as by heptadecyl-CoA, a potent competitive inhibitor
Joseph L Dixon et al.
Biochimica et biophysica acta, 1841(1), 34-43 (2013-08-31)
We provide novel insights into the function(s) of β-carotene-15,15'-oxygenase (CMOI) during embryogenesis. By performing in vivo and in vitro experiments, we showed that CMOI influences not only lecithin:retinol acyltransferase but also acyl CoA:retinol acyltransferase reaction in the developing tissues at
H Eltahlawy et al.
Archives of insect biochemistry and physiology, 64(3), 120-130 (2007-02-13)
The control of pheromone biosynthesis by the neuropeptide PBAN was investigated in the moth Heliothis virescens. When decapitated females were injected with [2-(14)C] acetate, females co-injected with PBAN produced significantly greater quantities of radiolabeled fatty acids in their pheromone gland

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