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C5459

Sigma-Aldrich

N-Carbethoxyphthalimide

96%

Synonym(s):

N-Ethoxycarbonylphthalimide, Ethyl 1,3-dioxo-2-isoindolinecarboxylate, Ethyl phthalimide-N-carboxylate

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About This Item

Empirical Formula (Hill Notation):
C11H9NO4
CAS Number:
22509-74-6
Molecular Weight:
219.19
Beilstein/REAXYS Number:
196340
EC Number:
245-048-5
MDL number:
MFCD00005893
UNSPSC Code:
12352100
PubChem Substance ID:
24892787
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

100

assay

96%

form

crystals

mp

90-92 °C (lit.)

SMILES string

CCOC(=O)N1C(=O)c2ccccc2C1=O

InChI

1S/C11H9NO4/c1-2-16-11(15)12-9(13)7-5-3-4-6-8(7)10(12)14/h3-6H,2H2,1H3

InChI key

VRHAQNTWKSVEEC-UHFFFAOYSA-N

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1 of 4

This Item
565788565780565749
β-Secretase inhibitor ≥97% (HPLC), powder

S4562

β-Secretase inhibitor

β-Secretase Inhibitor IV β-Secretase Inhibitor IV, CAS 797035-11-1, is a cell-permeable inhibitor that binds to BACE-1 active site and blocks its proteolytic activity (IC₅₀ = 15 nM for human BACE-1).

565788

β-Secretase Inhibitor IV

β-Secretase Inhibitor III The β-Secretase Inhibitor III controls the biological activity of β-Secretase. This small molecule/inhibitor is primarily used for Neuroscience applications.

565780

β-Secretase Inhibitor III

β-Secretase Inhibitor II The β-Secretase Inhibitor II, also referenced under CAS 263563-09-3, controls the biological activity of β-Secretase. This small molecule/inhibitor is primarily used for Neuroscience applications.

565749

β-Secretase Inhibitor II

form

powder

form

solid

form

lyophilized

form

solid

assay

≥97% (HPLC)

assay

≥98% (HPLC)

assay

≥95% (HPLC)

assay

≥95% (HPLC)

Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

100

mol wt

~_1.65 kDa

mol wt

-

mol wt

-

mol wt

-

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

−20°C

solubility

DMSO: soluble

solubility

DMSO: 100 mg/mL

solubility

DMSO: 1 mg/mL

solubility

DMSO: 5 mg/mL

Application

Used to protect amine functional groups.[1]

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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    Certificates of Analysis (COA)

    Lot/Batch Number
    MKCN0902
    MKCH0428
    STBH7834
    MKCD3852
    MKCB1455V

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    Jungmi Lee et al.
    Analytica chimica acta, 1022, 89-95 (2018-05-08)
    Amyloid-β (Aβ) is generated by proteolytic processing of amyloid precursor protein (APP) by beta-secretase (BACE-1) and gamma-secretase. Amyloid-β is responsible for the formation of senile plaques in Alzheimer's disease (AD). Consequently, inhibition of β-secretase (BACE-1), a rate-limiting enzyme in the
    Hans Hilpert et al.
    Journal of medicinal chemistry, 56(10), 3980-3995 (2013-04-18)
    An extensive fluorine scan of 1,3-oxazines revealed the power of fluorine(s) to lower the pKa and thereby dramatically change the pharmacological profile of this class of BACE1 inhibitors. The CF3 substituted oxazine 89, a potent and highly brain penetrant BACE1
    beta-secretase inhibitor; a promising novel therapeutic drug in Alzheimer?s disease
    Menting KW, et al.
    Frontiers in Aging Neuroscience, 6, 165-165 (2014)
    S Sinha et al.
    Nature, 402(6761), 537-540 (1999-12-11)
    Proteolytic processing of the amyloid precursor protein (APP) generates amyloid beta (Abeta) peptide, which is thought to be causal for the pathology and subsequent cognitive decline in Alzheimer's disease. Cleavage by beta-secretase at the amino terminus of the Abeta peptide
    Patty C Kandalepas et al.
    Acta neuropathologica, 126(3), 329-352 (2013-07-04)
    β-Site amyloid precursor protein (APP) cleaving enzyme-1 (BACE1) is the β-secretase that initiates Aβ production in Alzheimer's disease (AD). BACE1 levels are increased in AD, which could contribute to pathogenesis, yet the mechanism of BACE1 elevation is unclear. Furthermore, the
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