Phytosphingosine Chemical Properties

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).

pka

11.91±0.45(Predicted)

form 

White to off-white solid.

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℃

Safety Information

WGK Germany 

1

HS Code 

29221990

Phytosphingosine Usage And Synthesis

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 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]

Chemical Properties

Off-White Solid

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.

Uses

Phytosphingosine is a natural anti-microbial compound and it is involved in several cellular processes such as cell differentiation and anti-inflammation.

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

Not classified

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

Phytosphingosine(554-62-1)Related Product Information

• TRILAURIN
• HISTONE
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• beta-Sitosterol
• phytosphingosine
• Phytic acid
• Phytol
• Calcium phytate
• PHYTOSTEROLS
• N-HEXANOYL-PHYTOSPHINGOSINE
• N-(6-[(7-NITRO-2-1,3-BENZOXADIAZOL-4-YL)AMINO]CAPROYL)-PHYTOSPHINGOSINE
• N-ACETYL-PHYTOSPHINGOSINE
• N-TETRACOSANOYL-PHYTOSPHINGOSINE
• N-Stearoyl-phytosphingosine
• Phytosphingosine
• YEAST N-08:0 PHYTOSPHINGOSINE,N-OCTANOYL-PHYTOSPHINGOSINE (SACCHAROMYCES CEREVISIAE),N-OCTANOYL-PHYTOSPHINGOSINE
• alpha-Hydroxyoctadecanoyl-phytosphingosine
• Ceramides