Identification | Back Directory | [Name]
PHYTOSPHINGOSINE | [CAS]
554-62-1 | [Synonyms]
PHYTOSPHINGOSINE 4-HYDROXYSPHINGANINE C18-Phytosphingosine 4D-Hydroxysphinganine 4-D-Hydroxysphinganine D-ribo-Phytosphingosine D-threo-Phytosphingosine (4R)-4-Hydroxysphinganine PHYTOSPHINGOSINE HYDROCHLORIDE ribophytosphingosine hydrochloride D-Ribo-2-aminooctadecane-1,3,4-triol (2S,3S,4R)-2-Amino-1,3,4-octadecanetriol (2S,3S,4R)-2-aminooctadecane-1,3,4-triol d-ribo-1,3,4-trihydroxy-2-aminooctadecane (2S,3S,4R)-2-azanyloctadecane-1,3,4-triol 1,3,4-Octadecanetriol,2-amino-, (2S, 3S, 4R)- (2S, 3S, 4R)-2-AMINO-1,3,4-OCTADECANETRIOL 4-HYDROXYSPHINGANINE | [EINECS(EC#)]
205-516-1 | [Molecular Formula]
C18H39NO3 | [MDL Number]
MFCD02259274 | [MOL File]
554-62-1.mol | [Molecular Weight]
317.51 |
Chemical Properties | Back Directory | [Melting point ]
102 °C | [Boiling point ]
483.7±40.0 °C(Predicted) | [density ]
0.983 | [vapor pressure ]
0.2Pa at 20℃ | [refractive index ]
9 ° (C=1, Pyridine) | [storage temp. ]
−20°C
| [solubility ]
Soluble in Ethanol (up to 2 mg/ml). | [form ]
White to off-white solid. | [pka]
11.91±0.45(Predicted) | [color ]
White | [Water Solubility ]
2.6mg/L at 20℃ | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in ethanol may be stored at -20°C for up to 1 month. | [InChI]
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 | [InChIKey]
AERBNCYCJBRYDG-KSZLIROESA-N | [SMILES]
C(O)[C@H](N)[C@H](O)[C@H](O)CCCCCCCCCCCCCC | [LogP]
6.2 at 22℃ | [Uses]
phytosphingosine is a sphingolipid that can improve the overall condition of skin and hair. Some sources site anti-microbial and anti-inflammatory properties. Research indicates similar activity to retinoic acid, in which case it may be particularly beneficial for aging and photo-aging skin. |
Hazard Information | Back Directory | [Chemical Properties]
Off-White Solid | [Usage]
Phytosphingosine is a natural anti-microbial compound and it is involved in several cellular processes such as cell differentiation and anti-inflammation. | [Description]
Phytosphingosine is a sphingolipid with a hydroxyl group at the C4 position that is found mainly in fungi and plants but also in animals, including humans.1,2 It is metabolized to odd-numbered fatty acids with 2-hydroxy palmitic acid (Item No. 22679) as an intermediate.3 Phytosphingosine dose-dependently induces cell death of CHO cells and inhibits carbachol-induced activation of phospholipase D (PLD) in CHO cells transfected with C. elegans muscarinic acetylcholine receptors.4 It is essential in the heat stress response in S. cerevisiae.5 [Matreya, LLC. Catalog No. 1330] | [Definition]
ChEBI: Phytosphingosine is a sphingoid, an amino alcohol and a triol. It has a role as a Saccharomyces cerevisiae metabolite and a mouse metabolite. It is functionally related to a N-acyl-beta-D-galactosylphytosphingosine and a sphinganine. It is a conjugate base of a phytosphingosine(1+). | [Origin]
In 1884, chemist J.L.W coined the word phytosphingosine, which was taken from the term “sphingoid”, a major component in all biological membranes. There are four types of sphingoid bases and phytosphingosine is one of them. Phytosphingosine is a widely distributed natural sphingoid base and found in fungi, plants, and animals. | [Flammability and Explosibility]
Notclassified | [Veterinary Drugs and Treatments]
Phytosphingosine is a unique topical antiseborrheic compound. It is in a class called ceramides which are waxy materials meant to meant
to mimic the normal lipid composition of the stratum corneum. It may also have some antiinflammatory and antimicrobial properties. | [References]
1) Fischer et al. (2012), Antibacterial activity of sphingoid bases and fatty acids against Gram-positive and Gram-negative bacteria; Antimicrob. Agents Chemother., 56 1157
2) Fischer et al. (2013), Sphingoid bases are taken up by Escherichia coli and Staphylococcus aureus and induce ultrastructural damage; Skin Pharmacol. Physiol., 26 36 |
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