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(2S,3R,E)-2-Amino-4-icosene-1,3-diol

CAS No.
6918-49-6
Chemical Name:
(2S,3R,E)-2-Amino-4-icosene-1,3-diol
Synonyms
C20-Sphingosine;Eicosaphingenine;Eicosasphingenine;Gangliosphingosine;Sphingosine (d20:1);20-Carbon-sphingosine;D-erythro-Sphingosine C-20;(2S,3R,4E)-4-Icosasphingenine;D-erythro-Sphingosine (d20:1);Sphingosine (d20:1) (Standard)
CBNumber:
CB82148391
Molecular Formula:
C20H41NO2
Molecular Weight:
327.55
MDL Number:
MFCD08703032
MOL File:
6918-49-6.mol
MSDS File:
SDS
Last updated:2026-05-28 03:50:19

(2S,3R,E)-2-Amino-4-icosene-1,3-diol Properties

storage temp. -20°C
solubility DMF: 10 mg/ml; DMSO: 2 mg/ml; Ethanol: Miscible
form A crystalline solid
color White to off-white
BRN 3547228
InChI 1S/C20H41NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)19(21)18-22/h16-17,19-20,22-23H,2-15,18,21H2,1H3/b17-16+/t19-,20+/m0/s1
InChIKey HTJSZHKGNMXZJN-YIVRLKKSSA-N
SMILES OC[C@@](N)([H])[C@]([H])(O)/C=C/CCCCCCCCCCCCCCC
UNSPSC Code 12352211
NACRES NA.25

SAFETY

Risk and Safety Statements

Symbol(GHS)  Exclamation Mark (GHS07)
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P321-P362+P364-P332+P313-P337+P313-P403+P233-P405-P501
WGK Germany  3
Storage Class 11 - Combustible Solids
NFPA 704
0
2 0

(2S,3R,E)-2-Amino-4-icosene-1,3-diol price More Price(19)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 07768 (2S,3R,4E)-2-Amino-4-eicosene-1,3-diol ≥98.0% (TLC) 6918-49-6 10mg $203 2023-06-20 Buy
Sigma-Aldrich 07768 (2S,3R,4E)-2-Amino-4-eicosene-1,3-diol ≥98.0% (TLC) 6918-49-6 50mg $867 2023-01-07 Buy
Cayman Chemical 10007903 Sphingosine (d20:1) ≥98% 6918-49-6 500μg $37 2026-04-30 Buy
Cayman Chemical 10007903 Sphingosine (d20:1) ≥98% 6918-49-6 1mg $69 2026-04-30 Buy
Cayman Chemical 10007903 Sphingosine (d20:1) ≥98% 6918-49-6 5mg $194 2026-04-30 Buy
Product number Packaging Price Buy
07768 10mg $203 Buy
07768 50mg $867 Buy
10007903 500μg $37 Buy
10007903 1mg $69 Buy
10007903 5mg $194 Buy

(2S,3R,E)-2-Amino-4-icosene-1,3-diol Chemical Properties, Uses, Production

Description

Sphingosines are long-chain base precursors of cellular sphingolipids used directly in the synthesis of ceramide, which in combination with sialic acid forms ganglioside. Sphingosine can exist in four stereoisomers, however only sphingosine occurs naturally. Compared to other sphingolipids throughout the body, which are predominantly composed of C-18 sphingosine, only central nervous system (CNS) gangliosides contain significant amounts of sphingosine. The concentration of sphingosine within mammalian brain gangliosides apparently increases with developmental maturation. Furthermore, the ratio of C-18 to C-20 sphingosine in the brain is thought to be related to some nervous system degeneration processes.

Uses

Sphingosine (d20:1) has been used as a reference substance in liquid chromatography/tandem mass spectrometry analysis to quantitatively analyze sphingolipids with C20- long chain bases in human central nervous tissue.

Uses

D-erythro-Sphingosine-C20 is an antagonist in cell-signaling functions however it displays an opposite modulation of cathepsin D.

Definition

ChEBI: C20 sphingosine is a sphingoid that is the C20 analogue of sphingosine. It has a role as a mouse metabolite. It is a sphingoid and an aminodiol. It is a conjugate base of a C20 sphingosine(1+).

General Description

Sphingosine (d20:1), also known as icosasphingosine, is a synthetic sphingosine with 20 carbon long chain bases (LCB). It is directly produced by the sphingolipid de novo synthesis pathway and not by hydrolysis of complex sphingolipids. In higher animals, it is one of the most abundant sphingoid bases of gangliosides.

Biochem/physiol Actions

Sphingosine (d20:1) or C20-sphingosine acts as an intermediate in the synthesis of ceramides, which are vital components of mammalian epidermis. It may be involved in regulation of epidermal differentiation. C20 long chain bases-containing sphingolipids might exhibit detrimental effect on protein homeostasis and neural functions.

References

[1] MANUELA VALSECCHI. Changes of Free Long-Chain Bases in Neuronal Cells During Differentiation and Aging in Culture[J]. Journal of Neurochemistry, 1996, 67 5: 1866-1871. DOI: 10.1046/j.1471-4159.1996.67051866.x
[2] SANDRO SONNINO  Vanna C. Ganglioside molecular species containing C18- and C20-sphingosine in mammalian nervous tissues and neuronal cell cultures[J]. Biochimica et Biophysica Acta (BBA) - Reviews on Biomembranes, 2000, 1469 2: Pages 63-77. DOI: 10.1016/s0005-2736(00)00210-8

103411-92-3
6918-49-6
Synthesis of (2S,3R,E)-2-Amino-4-icosene-1,3-diol from 4-Eicosene-1,3-diol, 2-azido-, [R-[R*,S*-(E)]]- (9CI)

(2S,3R,E)-2-Amino-4-icosene-1,3-diol Preparation Products And Raw materials

Raw materials

Preparation Products

(2S,3R,E)-2-Amino-4-icosene-1,3-diol Suppliers

Global Suppliers ( 44)
Supplier Tel Email Country ProdList Advantage
Yichang Zhongyitai Trading Co., Ltd. 0717-6449896 13886658719 root@zhongyitai.com China 1978 58
Sigma-Aldrich 021-61415566 800-8193336 orderCN@merckgroup.com China 51389 80
Shanghai EFE Biological Technology Co., Ltd. 021-65675885 18964387627 info@efebio.com China 9799 58
Shanghai YuanYe Biotechnology Co., Ltd. 15026964105 2881489226@qq.com China 89667 60
Chengdu Huachun Technology Co., Ltd 400-1166-196 15982826727 cdhxsj@163.com China 14571 60
Shanghai Hongye Biotechnology Co. Ltd 400-9205774 400-920-5774 sales@glpbio.cn China 6705 58
TargetMol Chemicals Inc. +1-781-999-5354; +1-00000000000 marketing@targetmol.com United States 32431 58
ChemeGen(Shanghai) Biotechnology Co.,Ltd. 18818260767 sales@chemegen.com China 11123 58
MedBioPharmaceutical Technology Inc 021-69568360 18916172912 order@med-bio.cn China 8137 58
TargetMol Chemicals Inc. 4008200310 15002144251 marketing@tsbiochem.com China 24951 58

View Latest Price from (2S,3R,E)-2-Amino-4-icosene-1,3-diol manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Sphingosine (d20:1) pictures 2026-04-21 Sphingosine (d20:1)
6918-49-6
$223.00-688.00 10g TargetMol Chemicals Inc.
(2S,3R,E)-2-Amino-4-icosene-1,3-diol D-erythro-sphingosine (C20 base)
C20-Sphingosine Eicosasphingenine Gangliosphingosine D-erythro-Sphingosine C-20 D-erythro-sphingosine (C20 base) (2S,3R,4E)-2-Amino-4-eicosene-1,3-diol (2S,3R,4E)-4-Icosasphingenine 20-Carbon-sphingosine D-erythro-Sphingosine (d20:1) Eicosaphingenine trans-D-erythro-2-Amino-4-eicosene-1,3-diol
D-erythro-sphingosine (C20 base)
D-ERYTHRO-SPHINGOSINE (C20 BASE)
;SPHINGOSINE (D20:1)
Sphingosine (d20:1) 4-Eicosene-1,3-diol, 2-amino-, (2S,3R,4E)- Sphingosine (d20:1)/D-erythro-C20-Sphingosine Sphingosine (d20:1) (Standard) 6918-49-6