ChemicalBook--->CAS DataBase List--->554-62-1

554-62-1

554-62-1 Structure

554-62-1 Structure
IdentificationBack 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 PropertiesBack 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 InformationBack 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. It is metabolized to odd-numbered fatty acids with 2-hydroxy palmitic acid (Item No. 22679) as an intermediate. 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. It is essential in the heat stress response in S. cerevisiae. [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
Safety DataBack Directory
[WGK Germany ]

1
[HS Code ]

29221990
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