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Merck
CN

810215P

Avanti

C12-NBD Phytosphingosine

Avanti Research™ - A Croda Brand

Synonym(s):

N-(NBD-Aminolauroyl)phytosphingosine, N-[12-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]dodecanoyl]-phytosphingosine

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About This Item

Empirical Formula (Hill Notation):
C36H63N5O7
CAS Number:
388566-94-7
Molecular Weight:
677.91
MDL number:
MFCD02259274
UNSPSC Code:
12352211
NACRES:
NA.25

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Product Name

C12-NBD Phytosphingosine, Avanti Research™ - A Croda Brand

SMILES string

N[C@H]([C@H](O)[C@H](O)CCCCCCCCCCCCCC)CO

InChI

1S/C18H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17(21)18(22)16(19)15-20/h16-18,20-22H,2-15,19H2,1H3/t16-,17+,18-/m0/s1

InChI key

AERBNCYCJBRYDG-KSZLIROESA-N

assay

>99% (TLC)

form

powder

shipped in

dry ice

storage temp.

−20°C

description

N-[12-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]dodecanoyl]-phytosphingosine

packaging

pkg of 1 × 50 μg (810215P-50ug)

manufacturer/tradename

Avanti Research™ - A Croda Brand

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General description

C12-NBD Phytosphingosine is a fluorescent derivative of the naturally occurring lipid compound, phytosphingosine which is localised in skin, kidney and intestines.
Phytosphingosine is a ceramide molecule localized to the stratum corneum.

Application

C12-NBD Phytosphingosine has been used as a substrate in ceramidase activity assay to study enzyme activity.
C12-NBD phytosphingosine has been used as a substrate to assay ceramidase activity.

Biochem/physiol Actions

In vitro studies using human epidermis model shows that melanin production is prevented by phytosphingosine. Hence, it is widely used in cosmetics.
Phytosphingosine (PHS) is a sphingoid lipid molecule which is known to exhibit antimicrobial and anti-inflammatory action. PHS can has the ability to increase the production of keratinocyte differentiation marker proteins, such as transglutaminase 1 and involucrin, that are responsible for the development of cornifed envelope. PHS metabolism results in the formation of glycerophospholipids, sphingolipids and even-numbered fatty acids which mainly include palmitic acid.

Packaging

5 mL Amber Glass Screw Cap Vial (810215P-50ug)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class

11 - Combustible Solids

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Phytosphingosine and sphingosine ceramide headgroup hydrogen bonding: structural insights through thermotropic hydrogen/deuterium exchange
Rerek ME, et al.
The Journal of Physical Chemistry B, 105(38), 9355-9362 (2001)
Anti-melanogenic activity of phytosphingosine via the modulation of the microphthalmia-associated transcription factor signaling pathway
Jang EL, et al.
Journal of Dermatological Science, 87(1), 19-28 (2017)
Fluorescent and Luminescent Probes for Biological Activity (1999)
Hyun Kyung Choi et al.
Archives of dermatological research, 309(10), 795-803 (2017-09-25)
Phytosphingosine (PHS) is a sphingoid that is a key component of phytoceramides NP, AP and EOP. PHS has been known to have anti-inflammation and antimicrobial activities and to stimulate epidermal differentiation. In addition, it is reported that PHS treatment notably
Li-Yu Chen et al.
Nature communications, 6, 6030-6030 (2015-01-17)
Turgor pressure plays pivotal roles in the growth and movement of walled cells that make up plants and fungi. However, the molecular mechanisms regulating turgor pressure and the coordination between turgor pressure and cell wall remodelling for cell growth remain
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