Sphingosine (d16:1)
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Hodoodo CAT#: H464062

CAS#: 6982-09-8

Description: Sphingosine (d16:1) is an atypical sphingolipid formed by a series of enzymatic steps beginning with the condensation of myristoyl-CoA and serine via serine palmitoyltransferase long-chain base subunit 3 (SPTLC3), an SPT subunit that prefers myristoyl-CoA over palmitoyl-CoA. Sphingosine d16:1 is present in its free form at low levels in human plasma and as the sphingoid base in a variety of plasma sphingolipid species, including sphingosine-1-phosphate, ceramides, and sphingomyelins, as well as brain cerebrosides, at lower levels compared with the typical d18:1 sphingoid base. Sphingosine (d16:1) inhibits PKC in a mixed micelle activity assay. It reduces the production of superoxide induced by phorbol 12-myristate 13-acetate in isolated human neutrophils and reduces the growth of CHO cells (IC50s = 1 and 3.2 µM, respectively). Plasma levels of sphingolipids containing sphingosine (d16:1) are associated with dietary intake of saturated fatty acids and protein in ethnic Chinese individuals. Plasma levels of sphingolipids containing sphingosine (d16:1) are decreased in patients with type 2 diabetes.


Chemical Structure

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Sphingosine (d16:1)
CAS# 6982-09-8

Theoretical Analysis

Hodoodo Cat#: H464062
Name: Sphingosine (d16:1)
CAS#: 6982-09-8
Chemical Formula: C16H33NO2
Exact Mass: 271.25
Molecular Weight: 271.450
Elemental Analysis: C, 70.80; H, 12.25; N, 5.16; O, 11.79

Price and Availability

Size Price Availability Quantity
5mg USD 350 2 Weeks
10mg USD 550 2 Weeks
25mg USD 850 2 Weeks
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Synonym: Sphingosine (d16:1); Sphingosine-(d16:1); D-erythro-Sphingosine C-16; D-erythro-Sphingosine C16; D-erythro-Sphingosine C 16;

IUPAC/Chemical Name: (2S,3R,E)-2-aminohexadec-4-ene-1,3-diol

InChi Key: BTUSGZZCQZACPT-YYZTVXDQSA-N

InChi Code: InChI=1S/C16H33NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-16(19)15(17)14-18/h12-13,15-16,18-19H,2-11,14,17H2,1H3/b13-12+/t15-,16+/m0/s1

SMILES Code: OC[C@@H]([C@@H](/C=C/CCCCCCCCCCC)O)N

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO and DMF

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target: Sphingosine (d16:1) inhibits PKC in a mixed micelle activity assay. It reduces the production of superoxide induced by phorbol 12-myristate 13-acetate (PMA) in isolated human neutrophils and reduces the growth of CHO cells (IC50s = 1 and 3.2 µM, respectively).
In vitro activity: To be determined
In vivo activity: To be determined

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Soluble in DMSO 0.0 100.00

Preparing Stock Solutions

The following data is based on the product molecular weight 271.45 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: To be determined
In vitro protocol: To be determined
In vivo protocol: To be determined

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1: Chua XY, Chai YL, Chew WS, Chong JR, Ang HL, Xiang P, Camara K, Howell AR, Torta F, Wenk MR, Hilal S, Venketasubramanian N, Chen CP, Herr DR, Lai MKP. Immunomodulatory sphingosine-1-phosphates as plasma biomarkers of Alzheimer's disease and vascular cognitive impairment. Alzheimers Res Ther. 2020 Sep 30;12(1):122. doi: 10.1186/s13195-020-00694-3. PMID: 32998767; PMCID: PMC7528375.

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5: Chew WS, Torta F, Ji S, Choi H, Begum H, Sim X, Khoo CM, Khoo EYH, Ong WY, Van Dam RM, Wenk MR, Tai ES, Herr DR. Large-scale lipidomics identifies associations between plasma sphingolipids and T2DM incidence. JCI Insight. 2019 Jun 4;5(13):e126925. doi: 10.1172/jci.insight.126925. PMID: 31162145; PMCID: PMC6629294.

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9: Morifuji M, Kitade M, Oba C, Fukasawa T, Kawahata K, Yamaji T, Manabe Y, Sugawara T. Milk Fermented by Lactic Acid Bacteria Enhances the Absorption of Dietary Sphingomyelin in Rats. Lipids. 2017 May;52(5):423-431. doi: 10.1007/s11745-017-4247-0. Epub 2017 Mar 29. PMID: 28357619.

10: Al Sazzad MA, Yasuda T, Murata M, Slotte JP. The Long-Chain Sphingoid Base of Ceramides Determines Their Propensity for Lateral Segregation. Biophys J. 2017 Mar 14;112(5):976-983. doi: 10.1016/j.bpj.2017.01.016. PMID: 28297656; PMCID: PMC5355484.

11: Morifuji M, Higashi S, Oba C, Ichikawa S, Kawahata K, Yamaji T, Itoh H, Manabe Y, Sugawara T. Milk Phospholipids Enhance Lymphatic Absorption of Dietary Sphingomyelin in Lymph-Cannulated Rats. Lipids. 2015 Oct;50(10):987-96. doi: 10.1007/s11745-015-4054-4. Epub 2015 Aug 2. PMID: 26233817.

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13: Russo SB, Tidhar R, Futerman AH, Cowart LA. Myristate-derived d16:0 sphingolipids constitute a cardiac sphingolipid pool with distinct synthetic routes and functional properties. J Biol Chem. 2013 May 10;288(19):13397-409. doi: 10.1074/jbc.M112.428185. Epub 2013 Mar 25. PMID: 23530041; PMCID: PMC3650378.

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