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] CAROL L FISCHER. Antibacterial activity of sphingoid bases and fatty acids against Gram-positive and Gram-negative bacteria.[J]. Antimicrobial Agents and Chemotherapy, 2012: 1157-1161. DOI:10.1128/aac.05151-11
[2] C L FISCHER. Sphingoid bases are taken up by Escherichia coli and Staphylococcus aureus and induce ultrastructural damage.[J]. Skin Pharmacology and Physiology, 2013, 26 1: 36-44. DOI:10.1159/000343175

Phytosphingosine(554-62-1)Related Product Information

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• PHYTOSTEROLS
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• N-ACETYL-PHYTOSPHINGOSINE
• N-TETRACOSANOYL-PHYTOSPHINGOSINE
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• YEAST N-08:0 PHYTOSPHINGOSINE,N-OCTANOYL-PHYTOSPHINGOSINE (SACCHAROMYCES CEREVISIAE),N-OCTANOYL-PHYTOSPHINGOSINE
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