| Stereochemistry | EPIMERIC |
| Molecular Formula | C18H39NO3.C3H6O3 |
| Molecular Weight | 407.5851 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(O)C(O)=O.CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@@H](N)CO
InChI
InChIKey=ZXYOKWASAPQKDH-RXQQAGQTSA-N
InChI=1S/C18H39NO3.C3H6O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17(21)18(22)16(19)15-20;1-2(4)3(5)6/h16-18,20-22H,2-15,19H2,1H3;2,4H,1H3,(H,5,6)/t16-,17+,18-;/m0./s1
| Molecular Formula | C18H39NO3 |
| Molecular Weight | 317.5072 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | C3H6O3 |
| Molecular Weight | 90.0779 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
Phytosphingosine is structural analog of sphingolipids and is classified as long-chain sphingoid base. Phytosphingosine significantly induced chromatin DNA fragmentation. Phytosphingosine caused strong induction of caspase-8 activity and caspase-independent Bax translocation to the mitochondria. It shows excellent clinical results in the context of skin care in acne, based on both anti-inflammatory and anti-microbial activity. Phytosphingosine is currently seen in a variety of products as a skin and hair conditioning agent. Phytosphingosine might serve as an effective melanogenesis inhibitor in melanocytes via the regulation of the MITF signaling pathways. Dietary supplementation of phytosphingosine decreases plasma cholesterol levels and enhances insulin sensitivity in men with the metabolic syndrome.
Originator
Approval Year
PubMed
Patents
Sample Use Guides
Jurkat and NCI-H460 cells were treated with 5 or 10 ug/ml phytosphingosine, respectively, for the 2, 5, 10, 30, 60, 120 min. phytosphingosine treatment
led to a dramatic down-regulation of phosphorylated ERK1/2. The phosphorylated ERK started to diminish within 2 min of the phytosphingosine treatment.