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554-62-1 Usage

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.

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

Check Digit Verification of cas no

The CAS Registry Mumber 554-62-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,5 and 4 respectively; the second part has 2 digits, 6 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 554-62:
(5*5)+(4*5)+(3*4)+(2*6)+(1*2)=71
71 % 10 = 1
So 554-62-1 is a valid CAS Registry Number.
InChI:InChI=1/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

554-62-1 Well-known Company Product Price

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  • TCI America

  • (P1765)  Phytosphingosine  >98.0%(T)

  • 554-62-1

  • 1g

  • 820.00CNY

  • Detail
  • TCI America

  • (P1765)  Phytosphingosine  >98.0%(T)

  • 554-62-1

  • 5g

  • 2,140.00CNY

  • Detail

554-62-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name phytosphingosine

1.2 Other means of identification

Product number -
Other names (4R)-4-Hydroxysphinganine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:554-62-1 SDS

554-62-1Synthetic route

(2S,3S,4R,5Z)-2-azido-3,4-dibenzyloxy-5-octadecen-1-ol
471891-18-6

(2S,3S,4R,5Z)-2-azido-3,4-dibenzyloxy-5-octadecen-1-ol

D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal96%
(S)-tert-butyl 4-[(1S,2R)-1,2-dihydroxyhexadecyl]-2,2-dimethyloxazolidine-3-carboxylate
124127-36-2

(S)-tert-butyl 4-[(1S,2R)-1,2-dihydroxyhexadecyl]-2,2-dimethyloxazolidine-3-carboxylate

D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

Conditions
ConditionsYield
With water; trifluoroacetic acid for 0.25h;95%
With trifluoroacetic acid In water at 20℃; for 0.5h; Hydrolysis;92%
With trifluoroacetic acid In water68%
With trifluoroacetic acid In water for 1h; Hydrolysis;
With trifluoroacetic acid at 20℃; for 0.333333h;
(2S,3S,4R)-2-azido-1,3,4-octadecanetriol
117168-59-9

(2S,3S,4R)-2-azido-1,3,4-octadecanetriol

D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran 1.) 30 min, RT; 2.) 1 h, reflux;95%
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 48h;94%
With pyridine; hydrogen sulfide; water Ambient temperature;87%
(2S,3S,4R)-2-azidooctadec-6-yne-1,3,4-triol

(2S,3S,4R)-2-azidooctadec-6-yne-1,3,4-triol

D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol Ambient temperature;93%
(2S,3S,4R)-2-[(R)-1-phenylethylamino]octadecane-1,3,4-triol
925222-46-4

(2S,3S,4R)-2-[(R)-1-phenylethylamino]octadecane-1,3,4-triol

D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

Conditions
ConditionsYield
With hydrogen; palladium dihydroxide In ethanol at 20℃; under 5171.48 Torr;92%
(2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-phthalimido-3-hydroxy-octadecan-4-yl benzoate
1094213-81-6

(2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-phthalimido-3-hydroxy-octadecan-4-yl benzoate

D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

Conditions
ConditionsYield
Stage #1: (2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-phthalimido-3-hydroxy-octadecan-4-yl benzoate With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;
Stage #2: With hydrazine In methanol for 7h; Reflux; Inert atmosphere;
89%
(2S,3S,4R)-2-amino-1-benzoyloxy-octadecane-3,4-diol
111394-76-4, 111466-47-8

(2S,3S,4R)-2-amino-1-benzoyloxy-octadecane-3,4-diol

D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

Conditions
ConditionsYield
With potassium hydroxide In methanol 22 deg C, 12 h. then 60 deg C, 3 h.;85%
tert-butyl [(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]carbamate
175696-50-1

tert-butyl [(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]carbamate

D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

Conditions
ConditionsYield
With trifluoroacetic acid In water at 20℃; for 0.5h;82%
With trifluoroacetic acid In water at 20℃; for 0.5h; Inert atmosphere;82%
With trifluoroacetic acid at 20℃; for 0.5h;43%
(2R,3S,4R)-2-amino-3-hydroxyoctadecane-1,4-lactone hydrochloride

(2R,3S,4R)-2-amino-3-hydroxyoctadecane-1,4-lactone hydrochloride

D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 72h; Heating;82%
(2S,3S,4R)-2-benzylamino-1,3,4-dihydroxyoctadecane
219697-93-5

(2S,3S,4R)-2-benzylamino-1,3,4-dihydroxyoctadecane

D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

Conditions
ConditionsYield
With hydrogen; palladium dihydroxide In ethanol under 2585.74 Torr; for 16h;80%
With hydrogen; palladium dihydroxide In methanol Yield given;
(2S,3S,4R)-(2,3-bis-benzyloxy-1-hydroxymethyl-heptadecyl)-carbamic acid benzyl ester

(2S,3S,4R)-(2,3-bis-benzyloxy-1-hydroxymethyl-heptadecyl)-carbamic acid benzyl ester

D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

Conditions
ConditionsYield
With 20% palladium hydroxide-activated charcoal; hydrogen In methanol at 20℃; under 2585.81 Torr; for 48h;80%
(3R,4S,5R)-3-Azido-4-hydroxy-5-tetradecyl-dihydro-furan-2-one
309946-71-2

(3R,4S,5R)-3-Azido-4-hydroxy-5-tetradecyl-dihydro-furan-2-one

D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 63 - 65℃; for 2h; Reduction;78%
C44H53N3O3
947747-31-1

C44H53N3O3

D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol66%
2-azido-3,4-O-isopropylidene-1-O-triphenylmethyl-D-arabino-octadecane-1,3,4-triol
600168-67-0

2-azido-3,4-O-isopropylidene-1-O-triphenylmethyl-D-arabino-octadecane-1,3,4-triol

D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

Conditions
ConditionsYield
Stage #1: 2-azido-3,4-O-isopropylidene-1-O-triphenylmethyl-D-arabino-octadecane-1,3,4-triol In methanol; acetic acid at 60℃;
Stage #2: With triphenylphosphine In pyridine; water Staudinger reaction;
65%
(2S,3S,4R)-2-azidooctadec-5-yne-1,3,4-triol
1233506-76-7

(2S,3S,4R)-2-azidooctadec-5-yne-1,3,4-triol

D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

Conditions
ConditionsYield
With Pearlman's catalist; hydrogen In methanol63%
(2S,3S,4R)-2-(p-tolylsulfonamido)-1,3,4-octadecanetriol
174272-23-2

(2S,3S,4R)-2-(p-tolylsulfonamido)-1,3,4-octadecanetriol

D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

Conditions
ConditionsYield
With sodium tetrahydroborate; 1,5-dimethoxynaphthalene In ethanol; water for 10h; Ambient temperature; Irradiation;62.6%
C32H64N4O4SSi
1643949-12-5

C32H64N4O4SSi

D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

Conditions
ConditionsYield
Stage #1: C32H64N4O4SSi With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 65℃; Inert atmosphere;
Stage #2: With water; sodium hydroxide In tetrahydrofuran at 0℃; Inert atmosphere;
57%
(4S,5R)-4-((S)-1-Azido-2-trityloxy-ethyl)-2,2-dimethyl-5-((Z)-tetradec-1-enyl)-[1,3]dioxolane

(4S,5R)-4-((S)-1-Azido-2-trityloxy-ethyl)-2,2-dimethyl-5-((Z)-tetradec-1-enyl)-[1,3]dioxolane

D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; palladium on activated charcoal In methanol; chloroform; water52%
(2S,3S,4R)-2-(phthalimido)-octadecane-1,3,4-triol
13265-71-9

(2S,3S,4R)-2-(phthalimido)-octadecane-1,3,4-triol

D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

Conditions
ConditionsYield
With hydrazine hydrate In ethanol
(+)-2-Cyclohexanoylamino-1,3,4-trihydroxy-octadecan
409085-68-3

(+)-2-Cyclohexanoylamino-1,3,4-trihydroxy-octadecan

D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

Conditions
ConditionsYield
With methanol; sulfuric acid
(2S,3S,4R)-2-(benzylamino)octadecane-1,3,4-triol
70287-09-1

(2S,3S,4R)-2-(benzylamino)octadecane-1,3,4-triol

D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal
(2S,3S,4R)-2-Hydrazino-octadecane-1,3,4-triol; hydrochloride
127924-67-8

(2S,3S,4R)-2-Hydrazino-octadecane-1,3,4-triol; hydrochloride

D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

Conditions
ConditionsYield
With hydrogen; platinum(IV) oxide In ethanol; water for 24h;
N-[(1S,2S,3R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2,3-dihydroxy-heptadecyl]-benzamide
157117-30-1

N-[(1S,2S,3R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2,3-dihydroxy-heptadecyl]-benzamide

D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 95℃; for 12h; Yield given;
[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-ethyl]-carbamic acid tert-butyl ester
181824-87-3

[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-ethyl]-carbamic acid tert-butyl ester

D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

Conditions
ConditionsYield
With potassium hydroxide; trifluoroacetic acid 2.) MeOH; Yield given. Multistep reaction;
(1R,4'S,5'S)-1-<4'-(t-butyldiphenylsilyl)oxymethyl-2'-phenyl-4',5'-dihydrooxazol-5'-yl>pentadecan-1-ol
157117-26-5

(1R,4'S,5'S)-1-<4'-(t-butyldiphenylsilyl)oxymethyl-2'-phenyl-4',5'-dihydrooxazol-5'-yl>pentadecan-1-ol

D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide 1.) THF, water, room temperature, 5 h, 2.) THF, water, ethanol, 95 deg C, 12 h; Yield given; Multistep reaction;
Multi-step reaction with 3 steps
1: 4N HCl / tetrahydrofuran / 24 h / Ambient temperature
2: aq. NaOH / Ambient temperature
3: NaOH / aq. ethanol / 12 h / 95 °C
View Scheme
(4S,5S)-5-Azido-4-((R)-1-benzyloxy-pentadecyl)-2-(4-methoxy-phenyl)-[1,3]dioxane
603132-05-4

(4S,5S)-5-Azido-4-((R)-1-benzyloxy-pentadecyl)-2-(4-methoxy-phenyl)-[1,3]dioxane

D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol
methanol
67-56-1

methanol

(2S,3S,4R,2'R)-2-(2'-hydroxy-9'Z-ene-tetracosanoylamino)-octadecane-1,3,4-triol

(2S,3S,4R,2'R)-2-(2'-hydroxy-9'Z-ene-tetracosanoylamino)-octadecane-1,3,4-triol

A

D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

B

methyl 2-hydroxy-9Z-ene-tetracosanate

methyl 2-hydroxy-9Z-ene-tetracosanate

Conditions
ConditionsYield
With hydrogenchloride at 60℃; for 6h;
methanol
67-56-1

methanol

2,3-dihydroxy-N-[(1S,2S,3R)-2,3-dihydroxy-1-(hydroxymethyl)heptadecyl]tetracosanamide

2,3-dihydroxy-N-[(1S,2S,3R)-2,3-dihydroxy-1-(hydroxymethyl)heptadecyl]tetracosanamide

A

D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

B

methyl 2,3-dihydroxytetracosanoate

methyl 2,3-dihydroxytetracosanoate

Conditions
ConditionsYield
In water at 80℃; for 16h;
(2S,3S,4R)-2-azido-3,4-di-O-benzyl-1,3,4-octadecanetriol
202812-10-0

(2S,3S,4R)-2-azido-3,4-di-O-benzyl-1,3,4-octadecanetriol

D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

Conditions
ConditionsYield
With hydrogen; palladium dihydroxide In methanol
D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

ethyl trifluoroacetate,
383-63-1

ethyl trifluoroacetate,

2,2,2-trifluoro-N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]acetamide
354149-81-8

2,2,2-trifluoro-N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]acetamide

Conditions
ConditionsYield
In ethanol at 20℃; for 20h;100%
In ethanol at 20℃; for 12h; Inert atmosphere;92%
In ethanol at 25℃;90%
D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

(2S,3S,4R)-2-azido-1,3,4-octadecanetriol
117168-59-9

(2S,3S,4R)-2-azido-1,3,4-octadecanetriol

Conditions
ConditionsYield
With triflic azide; potassium carbonate; copper(II) sulfate In methanol; dichloromethane; water at 20℃; for 18h;100%
With copper(ll) sulfate pentahydrate; triflic azide; potassium carbonate In methanol; water at 20℃; Inert atmosphere;100%
With triflic azide; copper(II) sulfate In methanol; dichloromethane; water for 18h;98%
D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

(2S,3S,4R)-2-amino-1-((tert-butyldiphenylsilyl)oxy)octadecane-3,4-diol
1224436-75-2

(2S,3S,4R)-2-amino-1-((tert-butyldiphenylsilyl)oxy)octadecane-3,4-diol

Conditions
ConditionsYield
With pyridine regioselective reaction;100%
With pyridine
D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

tetrachlorophthalic anhydride
117-08-8

tetrachlorophthalic anhydride

(2S,3S,4R)-2-(tetrachlorophthalimido)-octadecan-1,3,4-triol
1535186-19-6

(2S,3S,4R)-2-(tetrachlorophthalimido)-octadecan-1,3,4-triol

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 150℃; for 0.166667h; Inert atmosphere;100%
In N,N-dimethyl-formamide at 150℃; for 0.0833333h; Inert atmosphere;
D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

1-hexacosanoic acid
506-46-7

1-hexacosanoic acid

hexacosanoic acid (2,3-dihydroxy-1-hydroxymethyl-heptadecyl) amide
182362-51-2

hexacosanoic acid (2,3-dihydroxy-1-hydroxymethyl-heptadecyl) amide

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 168h;100%
D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

benzoyl chloride
98-88-4

benzoyl chloride

(2S,3R,4R)-2-(N-benzoyl)amino-octadecane-1,3,4-triol
1987-40-2

(2S,3R,4R)-2-(N-benzoyl)amino-octadecane-1,3,4-triol

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 0.5h;99%
With triethylamine In tetrahydrofuran for 0.5h;99%
With sodium hydroxide; diethyl ether
D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

acetic anhydride
108-24-7

acetic anhydride

N,O,O,O-tetraacetyl-D-ribo-phytosphingosine
13018-48-9

N,O,O,O-tetraacetyl-D-ribo-phytosphingosine

Conditions
ConditionsYield
With pyridine; dmap for 18h; Ambient temperature;98%
With pyridine at 20℃;98%
With pyridine; dmap at 20℃; Acetylation;94%
D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

tert-butyl [(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]carbamate
175696-50-1

tert-butyl [(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]carbamate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 2h;98%
With sodium hydroxide In ethanol; water at 0 - 20℃; Inert atmosphere;96%
With potassium carbonate In methanol for 1h;95%
D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(2S, 3S, 4R)-2-[N-(9-fluorenylmethyloxycarbonyl)amino]octadecane-1,3,4-triol
1549685-07-5

(2S, 3S, 4R)-2-[N-(9-fluorenylmethyloxycarbonyl)amino]octadecane-1,3,4-triol

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 2.5h; Inert atmosphere;97%
D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

stearic acid
57-11-4

stearic acid

(2S,3S,4R)-2-(N-stearoylamino)octadecane-1,3,4-triol
34354-88-6

(2S,3S,4R)-2-(N-stearoylamino)octadecane-1,3,4-triol

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane96%
With potassium fluoride; sodium persulfate; 1,4-dimethyl-4H-1,2,4-triazol-1-ium chloride In tert-butyl methyl ether at 20℃; for 36h;84%
With pyridine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 40h;68%
D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

triflic azide
3855-45-6

triflic azide

(2S,3S,4R)-2-azido-1,3,4-octadecanetriol
117168-59-9

(2S,3S,4R)-2-azido-1,3,4-octadecanetriol

Conditions
ConditionsYield
96%
hexacosanoic acid 2,5-dioxo-pyrrolidin-1-yl ester
22102-68-7

hexacosanoic acid 2,5-dioxo-pyrrolidin-1-yl ester

D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

hexacosanoic acid (2,3-dihydroxy-1-hydroxymethyl-heptadecyl) amide
182362-51-2

hexacosanoic acid (2,3-dihydroxy-1-hydroxymethyl-heptadecyl) amide

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 50℃; for 14h;95%
In tetrahydrofuran94%
With triethylamine In tetrahydrofuran at 50℃; for 20h; Inert atmosphere;88%
D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

ethyl benzimidate hydrochloride
5333-86-8

ethyl benzimidate hydrochloride

2-phenyl-4-(S)-[(1R,2R)-1,2-dihydroxyhexadecyl]-1,3-oxazoline
572922-35-1

2-phenyl-4-(S)-[(1R,2R)-1,2-dihydroxyhexadecyl]-1,3-oxazoline

Conditions
ConditionsYield
With triethylamine In dichloromethane at 40℃; for 48h;95%
With triethylamine In dichloromethane at 40℃; for 48h;95%
D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

3-(isocyanatomethyl)heptane
20392-34-1

3-(isocyanatomethyl)heptane

C27H56N2O4

C27H56N2O4

Conditions
ConditionsYield
In tetrahydrofuran95%
D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

phenyl isocyanate
103-71-9

phenyl isocyanate

C25H44N2O4

C25H44N2O4

Conditions
ConditionsYield
In tetrahydrofuran95%
D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

C40H70N6O8

C40H70N6O8

kozupeptin A

kozupeptin A

Conditions
ConditionsYield
In chloroform at 20℃; for 6h;95%
In chloroform at 20℃; for 2.5h;51%
D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

behenic acid methyl ester
929-77-1

behenic acid methyl ester

(2S,3S,4R)-2-docosanoylamino-1,3,4-octadecanetriol
164576-03-8

(2S,3S,4R)-2-docosanoylamino-1,3,4-octadecanetriol

Conditions
ConditionsYield
With sodium ethanolate In ethanol at 55℃;94.1%
D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

2,2,2-trifluoro-N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]acetamide
354149-81-8

2,2,2-trifluoro-N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]acetamide

Conditions
ConditionsYield
With potassium carbonate In dichloromethane at 20℃; for 18h;94%
With potassium carbonate In dichloromethane at 20℃; for 18h;94%
With potassium carbonate In dichloromethane at 20℃; for 18h;94%
D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

15-(nonyloxy)pentadecanoic acid

15-(nonyloxy)pentadecanoic acid

15-(nonyloxy)pentadecanoic acid(2,3-dihydroxy-1-hydroxymethyl-heptadecyl)amide

15-(nonyloxy)pentadecanoic acid(2,3-dihydroxy-1-hydroxymethyl-heptadecyl)amide

Conditions
ConditionsYield
With triethylamine; p-toluenesulfonyl chloride In dichloromethane for 8h; Reflux;93.1%
D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

15-(undecyloxy)pentadecanoic acid

15-(undecyloxy)pentadecanoic acid

15-(undecyloxy)pentadecanoic acid(2,3-dihydroxy-1-hydroxymethyl-heptadecyl)amide

15-(undecyloxy)pentadecanoic acid(2,3-dihydroxy-1-hydroxymethyl-heptadecyl)amide

Conditions
ConditionsYield
With triethylamine; p-toluenesulfonyl chloride In dichloromethane for 8h; Reflux;92.8%
D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

15-(octadecanoyloxy)pentadecanoic acid

15-(octadecanoyloxy)pentadecanoic acid

15-(octadecanoyloxy)pentadecanoic acid(2,3-dihydroxy-1-hydroxymethyl-heptadecyl)amide

15-(octadecanoyloxy)pentadecanoic acid(2,3-dihydroxy-1-hydroxymethyl-heptadecyl)amide

Conditions
ConditionsYield
With triethylamine; p-toluenesulfonyl chloride In dichloromethane for 8h; Reflux;92.1%
D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

benzyl chloroformate
501-53-1

benzyl chloroformate

(2S,3R,4R)-2-benzyloxycarbonylamino-1,3,4-octadecanetriol
634587-38-5

(2S,3R,4R)-2-benzyloxycarbonylamino-1,3,4-octadecanetriol

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone at 20℃;92%
With sodium hydrogencarbonate In 1,4-dioxane at 20℃;90%
With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃;90%
With sodium hydrogencarbonate In 1,4-dioxane; ethyl acetate at 20℃;90%
With sodium carbonate In water; acetone at 20℃;
D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

1-hexacosanoic acid
506-46-7

1-hexacosanoic acid

C48H97NO4
871541-12-7

C48H97NO4

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 100℃; for 6h;92%
D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

n-butyl isocyanide
111-36-4

n-butyl isocyanide

C23H48N2O4

C23H48N2O4

Conditions
ConditionsYield
In tetrahydrofuran92%
D-ribo-phytosphingosine
554-62-1

D-ribo-phytosphingosine

15-acetoxypentadecanoic acid
69186-31-8

15-acetoxypentadecanoic acid

15-(acetoxy)pentadecanoic acid (2,3-dihydroxy-1-hydroxymethyl-heptadecyl)amide

15-(acetoxy)pentadecanoic acid (2,3-dihydroxy-1-hydroxymethyl-heptadecyl)amide

Conditions
ConditionsYield
With triethylamine; p-toluenesulfonyl chloride In dichloromethane for 8h; Reflux;92%

554-62-1Relevant articles and documents

-

Prostenik,M. et al.

, p. 651 - 655 (1965)

-

Phytoceramides and acylated phytosterol glucosides from Pterospermum acerifolium Willd. seed coat and their osteogenic activity

Dixit, Preety,Chand, Kailash,Khan, Mohd Parvez,Siddiqui, Jawed Akhtar,Tewari, Deepshikha,Ngueguim, Florence Tsofack,Chattopadhyay, Naibedya,Maurya, Rakesh

, p. 117 - 125 (2012)

Phytochemical investigation of seed coats of Pterospermum acerifolium afforded two phytoceramides (1, 2) and two acylated phytosterol glucosides (3, 4) together with five known compounds (5-9). Their structures were elucidated on the basis of extensive sp

Convergent evolution of bacterial ceramide synthesis

Ashley, Ben,Campopiano, Dominic J.,Chamberlain, Joshua D.,Coleman, Aimiyah,D’Emilia, Rachel,Fu, Larina,Guan, Ziqiang,Hansen, Matthew E. B.,Klein, Eric A.,Mohan, Eric C.,Nguyen, Hung,Stankeviciute, Gabriele,Tang, Peijun

, (2022/01/06)

The bacterial domain produces numerous types of sphingolipids with various physiological functions. In the human microbiome, commensal and pathogenic bacteria use these lipids to modulate the host inflammatory system. Despite their growing importance, their biosynthetic pathway remains undefined since several key eukaryotic ceramide synthesis enzymes have no bacterial homolog. Here we used genomic and biochemical approaches to identify six proteins comprising the complete pathway for bacterial ceramide synthesis. Bioinformatic analyses revealed the widespread potential for bacterial ceramide synthesis leading to our discovery of a Gram-positive species that produces ceramides. Biochemical evidence demonstrated that the bacterial pathway operates in a different order from that in eukaryotes. Furthermore, phylogenetic analyses support the hypothesis that the bacterial and eukaryotic ceramide pathways evolved independently. [Figure not available: see fulltext.]

Divergent total synthesis of D-ribo-phytosphingosine and L-ribo-phytosphingosine from D-ribose

Chun, Jong Soo,Hong, Seung Min,Jeon, Tae Hong,Park, Sook Jin,Son, Han Pyo,Jung, Jun Min,Choi, Young Jae,Kim, In Su,Jung, Young Hoon

, p. 8550 - 8556 (2016/12/09)

Divergent total synthesis of D-ribo-phytosphingosine (1) and L-ribo-phytosphingosine (2) was achieved from readily available D-ribose via cross-metathesis reaction, Wittig reaction, and diastereoselective amination reaction of allylic ethers using chlorosulfonyl isocyanate (CSI) as the key steps. As results, reactions of anti-1,2-dibenzyl ethers 11 and 16 with chlorosulfonyl isocyanate afforded exclusively anti-1,2-amino alcohols 12 and 17 with diastereoselectivity of 32:1 and 31:1 in 75% and 76% yields, respectively. These results could be explained by the neighboring group effect, leading to retention of stereochemistry.

Protein and peptide-free synthetic vaccines against streptococcus pneumoniae type 3

-

Paragraph 0099, (2015/03/31)

The present invention provides a protein- and peptide-free conjugate comprising a synthetic carbohydrate and a carrier molecule, wherein the synthetic carbohydrate is a Streptococcus pneumoniae type 3 capsular polysaccharide related carbohydrate and the carrier molecule is a glycosphingolipid. Said conjugate and pharmaceutical composition thereof are useful for immunization against diseases associated with Streptococcus pneumoniae, and more specifically against diseases associated with Streptococcus pneumoniae type 3.

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