CAS Number24967-27-9
Synonyms5-acetamido-2,6-anhydro-3,5-dideoxy-D-glycero-D-galactonon-2-enonic acid; 2,3,4-TRIMETHYL-3-PENTANOL; 5-acetamido-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enoic acid; N-acetyl-2,3-didehydro-2-deoxyneuraminic acid; 1,3-DEHYDRO-2-DEOXY-N-ACETYLNEURAMINIC ACID; 2,3-DEHYDRO-2-DEOXY-N-ACETYLNEURAMINIC ACID; 2,3-Dehydro-2-deoxy-N-acetylneuraminic AcidDANA; MFCD00057470; N-Acetyl-2,3-dehydro-2-deoxyneuraminic acid; 2,3-didehydro-2-deoxy-N-acetylneuraminic acid; 2-deoxy-2,3-dehydro-n-acetylneuraminicacid; EINECS 246-550-7
Molecular FormulaC11H17NO8
Molecular Weight291.25
Purity≥93 (TLC)%
Density1.58g/cm3
Boiling Point773.4ºC at 760 mmHg
Melting Point227-228ºC
Appearancepowder
EINECS246-550-7
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 24967-27-9 |
| Catalog No. | 2A-0201333 |
| Chinese Name | N-乙酰-2,3-二脱氢-2-脱氧神经氨酸 |
| Synonyms | 5-acetamido-2,6-anhydro-3,5-dideoxy-D-glycero-D-galactonon-2-enonic acid; 2,3,4-TRIMETHYL-3-PENTANOL; 5-acetamido-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enoic acid; N-acetyl-2,3-didehydro-2-deoxyneuraminic acid; 1,3-DEHYDRO-2-DEOXY-N-ACETYLNEURAMINIC ACID; 2,3-DEHYDRO-2-DEOXY-N-ACETYLNEURAMINIC ACID; 2,3-Dehydro-2-deoxy-N-acetylneuraminic AcidDANA; MFCD00057470; N-Acetyl-2,3-dehydro-2-deoxyneuraminic acid; 2,3-didehydro-2-deoxy-N-acetylneuraminic acid; 2-deoxy-2,3-dehydro-n-acetylneuraminicacid; EINECS 246-550-7 |
| Molecular Formula | C11H17NO8 |
| Molecular Weight | 291.25 |
| Purity | ≥93 (TLC) |
| Density | 1.58g/cm3 |
| Boiling Point | 773.4ºC at 760 mmHg |
| Melting Point | 227-228ºC |
| Appearance | powder |
| Storage Condition | <0°C; avoid heating |
| Application | N-acetyl-2,3-dehydro-2-deoxyneuraminic acid (Neu5Ac2en) is a potent neuraminidase (sialidase) inhibitor. N-acetyl-2,3-dehydro-2-deoxyneuraminic acid has inhibitory activity against human neuraminidase |
| EINECS | 246-550-7 |
| PubChem ID | 24894248 |
| MDL Number | MFCD00135810 |
| SMILES | CC(=O)N[C@@H]1[C@@H](O)C=C(O[C@H]1[C@H](O)[C@H](O)CO)C(O)=O |
| InChI | 1S/C11H17NO8/c1-4(14)12-8-5(15)2-7(11(18)19)20-10(8)9(17)6(16)3-13/h2,5-6,8-10,13,15-17H,3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,8+,9+,10+/m0/s1 |
| InChI Key | JINJZWSZQKHCIP-UFGQHTETSA-N |
| Beilstein/REAXYS | 8722455 |
| NACRES Code | NA.25 |
| UNSPSC | 12352201 |
| Hazard Symbols | transportation |
| MSDS | msds/85200_1_24967_27_9.pdf |
| Bioactivity | N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid (Neu5Ac2en) is a potent neuraminidase (sialidase) inhibitor. N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid shows inhibitory activities against human neuraminidase enzymes with IC50s of 143, 43, 61, and 74 μM for NEU1, NEU2, NEU3, and NEU4, respectively. Anti-influenza virus activity[1][2]. Related Catalog Signaling Pathways >> Anti-infection >> Influenza Virus Research Areas >> Infection In Vitro N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid (Neu5Ac2en) (10-100 μM) signifcantly inhibits sialidase activity in INS-1D cells[4]. In Vivo N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid (Neu5Ac2en) (10 mg/kg; i.p.; daily) attenuates pulmonary fibrosis in a mouse model[3]. Animal Model: Mice (Mouse model of pulmonary fibrosis)[3] Dosage: 10 mg/kg Administration: I.p.; daily (starting at day 10 after Bleomycin, and then euthanized at day 21) Result: Inhibition of sialidases starting at day 10 after bleomycin attenuates fibrosis. References [1]. Magesh S, et al. Design, synthesis, and biological evaluation of human sialidase inhibitors. Part 1: selective inhibitors of lysosomal sialidase (NEU1). Bioorg Med Chem Lett. 2008;18(2):532-537. [2]. Xiao A, et al. Sialidase-catalyzed one-pot multienzyme (OPME) synthesis of sialidase transition-state analogue inhibitors. ACS Catal. 2018;8(1):43-47. [3]. Karhadkar TR, et al. Sialidase inhibitors attenuate pulmonary fibrosis in a mouse model. Sci Rep. 2017;7(1):15069. Published 2017 Nov 8. [4]. Minami A, et al. The sialidase inhibitor 2,3-dehydro-2-deoxy-N-acetylneuraminic acid is a glucose-dependent potentiator of insulin secretion. Sci Rep. 2020;10(1):5198. Published 2020 Mar 23. Chemical & Physical Properties Density 1.58g/cm3 Boiling Point 773.4ºC at 760 mmHg Melting Point 227-228ºC Molecular Formula C11H17NO8 Molecular Weight 291.25500 Flash Point 421.6ºC Exact Mass 291.09500 PSA 156.55000 Vapour Pressure 1.27E-27mmHg at 25°C Index of Refraction 1.612 InChIKey JINJZWSZQKHCIP-UFGQHTETSA-N SMILES CC(=O)NC1C(O)C=C(C(=O)O)OC1C(O)C(O)CO |
| Use of | N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid (Neu5Ac2en) is a potent neuraminidase (sialidase) inhibitor. N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid shows inhibitory activities against human neuraminidase enzymes with IC50s of 143, 43, 61, and 74 μM for NEU1, NEU2, NEU3, and NEU4, respectively. Anti-influenza virus activity[1][2]. Properties Articles45 Name n-acetylneuraminic acid, 2,3-dehydro-2-deoxy-, sodium salt Synonym More Synonyms Biological Activity Description N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid (Neu5Ac2en) is a potent neuraminidase (sialidase) inhibitor. N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid shows inhibitory activities against human neuraminidase enzymes with IC50s of 143, 43, 61, and 74 μM for NEU1, NEU2, NEU3, and NEU4, respectively. Anti-influenza virus activity[1][2]. Related Catalog Signaling Pathways >> Anti-infection >> Influenza Virus Research Areas >> Infection In Vitro N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid (Neu5Ac2en) (10-100 μM) signifcantly inhibits sialidase activity in INS-1D cells[4]. References [1]. Magesh S, et al. Design, synthesis, and biological evaluation of human sialidase inhibitors. Part 1: selective inhibitors of lysosomal sialidase (NEU1). Bioorg Med Chem Lett. 2008;18(2):532-537. [2]. Xiao A, et al. Sialidase-catalyzed one-pot multienzyme (OPME) synthesis of sialidase transition-state analogue inhibitors. ACS Catal. 2018;8(1):43-47. [3]. Karhadkar TR, et al. Sialidase inhibitors attenuate pulmonary fibrosis in a mouse model. Sci Rep. 2017;7(1):15069. Published 2017 Nov 8. [4]. Minami A, et al. The sialidase inhibitor 2,3-dehydro-2-deoxy-N-acetylneuraminic acid is a glucose-dependent potentiator of insulin secretion. Sci Rep. 2020;10(1):5198. Published 2020 Mar 23. Chemical & Physical Properties Molecular Formula C11H17NO8 Exact Mass 291.09500 PSA 156.55000 Index of Refraction 1.612 InChIKey JINJZWSZQKHCIP-UFGQHTETSA-N |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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