| Identification | Back Directory | [Name]
10(S),17(S)-DiHDoHE | [CAS]
871826-47-0 | [Synonyms]
10(S),17(S)-DiHDHA
10(S),17(S)-DiHDoHE
10(S),17(S)-DiHDoHE Exclusive
4,7,11,13,15,19-Docosahexaenoic acid, 10,17-dihydroxy-, (4Z,7Z,10S,11E,13Z,15E,17S,19Z)- | [Molecular Formula]
C22H32O4 | [MDL Number]
MFCD18427937 | [MOL File]
871826-47-0.mol | [Molecular Weight]
360.487 |
| Chemical Properties | Back Directory | [storage temp. ]
Store at -20°C | [solubility ]
0.1 M Na2CO3: 1 mg/ml; DMF: Miscible; DMSO: Miscible; Ethanol: Miscible; PBS (pH 7.2): 0.5 mg/ml | [form ]
Solid | [color ]
White to off-white |
| Hazard Information | Back Directory | [Description]
Protectin D1 (also known as neuroprotectin D1 when produced in neuronal tissues) is a DHA-derived dihydroxy fatty acid that exhibits potent protective and anti-inflammatory activities.1,2,3 10(S),17(S)-DiHDHA is a DHA metabolite, also referred to as protectin DX (PDX).4 It is produced by an apparent double lipoxygenase (LO)-mediated reaction in murine peritonitis exudates, in suspensions of human leukocytes, or by soybean 15-LO incubated with DHA.1,4 It differs from protectin D1 with respect to the stereochemistry of the C-10 hydroxyl and the double bond configuration at the 13 and 15 positions. 10(S),17(S)-DiHDHA blocks neutrophil infiltration in murine peritonitis by 20-25% at a dose of 1 ng/mouse.1 It also inhibits platelet activation by both impairing thromboxane (TX) synthesis and TX receptor activation.4,5 | [Definition]
ChEBI: (4Z,7Z,10S,11E,13Z,15E,17S,19Z)-10,17-dihydroxydocosahexaenoic acid is a dihydroxydocosahexaenoic acid that is (4Z,7Z,11E,13Z,15E,19Z)-docosahexaenoic acid in which the two hydroxy substituents are located at positions 10 and 17 (the 10S,17S-stereoisomer). A natural isomer of protectin D1, one of the specialised proresolving mediators. It has a role as an anti-inflammatory agent and a human xenobiotic metabolite. It is a dihydroxydocosahexaenoic acid, a secondary allylic alcohol and a protectin. | [References]
1. Serhan, C.N., Gotlinger, K., Hong, S., et al. Anti-inflammatory actions of neuroprotectin D1/protectin D1 and its natural stereoisomers: Assignments of dihydroxy-containing docosatrienes J. Immunol. 176(3),1848-1859(2006).
2. Ariel, A., and Serhan, C.N. Resolvins and protectins in the termination program of acute inflammation Trends Immunol. 28(4),176-183(2007).
3. Schwab, J.M., Chiang, N., Arita, M., et al. Resolvin E1 and protectin D1 activate inflammation-resolution programmes Nature 447(7146),869-874(2007).
4. Chen, P., Fenet, B., Michaud, S., et al. Full characterization of PDX, a neuroprotectin/protectin D1 isomer, which inhibits blood platelet aggregation FEBS Lett. 583,3478-3484(2009).
5. Chen, P., Véricel, E., Lagarde, M., et al. Poxytrins, a class of oxygenated products from polyunsaturated fatty acids, potently inhibit blood platelet aggregation FASEB J. 25,382-388(2011). |
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