3-hexanoyl-NBD Cholesterol

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Category	Phospholipids
Catalog NO.	BPG-3271
Product Name	3-hexanoyl-NBD Cholesterol
CAS	201731-19-3
Molecular Formula	C39H58N4O5
Molecular Weight	662.90

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Description	3-hexanoyl-NBD cholesterol is a fluorescently-tagged cholesterol derivative with the hydrophilic NBD fluorophore attached to carbon 3. When incorporated in the membrane bilayers, the cholesterol is in the bilayers yet the fluorophore NBD is outside. It is used to study the metabolism of cholesterol derivative.
Synonyms	5-cholesten-3β-ol 6-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]caproate; 3-C6-NBD Cholesterol; NBD-6 Cholesterol; Cholest-5-en-3-ol (3β)-6-[(7-Nitro-2,1,3-benzoxadiazol-4-yl)amino]hexanoate; (3β,20R)-Cholest-5-en-3-yl 6-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]hexanoate; 3-C6-NBD Cholesterol
IUPAC Name	[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 6-[(4-nitro-2,1,3-benzoxadiazol-7-yl)amino]hexanoate
Canonical SMILES	CC(C)CCCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)OC(=O)CCCCCNC5=CC=C(C6=NON=C56)[N+](=O)[O-])C)C
InChI	InChI=1S/C39H58N4O5/c1-25(2)10-9-11-26(3)30-15-16-31-29-14-13-27-24-28(19-21-38(27,4)32(29)20-22-39(30,31)5)47-35(44)12-7-6-8-23-40-33-17-18-34(43(45)46)37-36(33)41-48-42-37/h13,17-18,25-26,28-32,40H,6-12,14-16,19-24H2,1-5H3/t26-,28+,29+,30-,31+,32+,38+,39-/m1/s1
InChIKey	YZAQIPGLFHPDPI-FIWRCADXSA-N
Boiling Point	736.3±70.0°C at 760 mmHg
Purity	≥98%
Density	1.2±0.1 g/cm3
Solubility	Soluble in DMF, DMSO, Ethanol
Appearance	Yellow to Orange Solid
Shelf Life	1 Year
Storage	Store at -20°C
Exact Mass	662.441
Hygroscopic	Yes
Light Sensitive	Yes
Percent Composition	C 70.66%, H 8.82%, N 8.45%, O 12.07%

References

1. Vázquez-Ríos AJ, Molina-Crespo Á, Bouzo BL, López-López R, Moreno-Bueno G, de la Fuente M. Exosome-mimetic nanoplatforms for targeted cancer drug delivery. J Nanobiotechnology. 2019 Jul 18;17(1):85. doi: 10.1186/s12951-019-0517-8. PubMed ID: 31319859.

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