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Sigma-Aldrich

L-(−)-α-Amino-ε-caprolactam hydrochloride

≥97.0% (AT)

Synonym(s):

(S)-3-Amino-hexahydro-2-azepinone hydrochloride, L-Lysine lactam hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C6H12N2O · HCl
CAS Number:
26081-07-2
Molecular Weight:
164.63
Beilstein/REAXYS Number:
4820243
MDL number:
MFCD02683418
UNSPSC Code:
12352005
PubChem Substance ID:
57647925
NACRES:
NA.22

assay

≥97.0% (AT)

form

solid

optical activity

[α]20/D −27±2°, c = 1% in H2O

optical purity

enantiomeric ratio: ≥99:1 (HPLC)

storage temp.

2-8°C

SMILES string

Cl[H].N[C@H]1CCCCNC1=O

InChI

1S/C6H12N2O.ClH/c7-5-3-1-2-4-8-6(5)9;/h5H,1-4,7H2,(H,8,9);1H/t5-;/m0./s1

InChI key

LWXJCGXAYXXXRU-JEDNCBNOSA-N

Application

L-(−)-α-Amino-ε-caprolactam hydrochloride can be used to introduce caprolactam moiety during the total synthesis of bengamides, which are bioactive compounds naturally found in marine sponges.

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)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Total synthesis of bengamide E
Liu W, et al.
Tetrahedron Letters, 43(8), 1373-1375 (2002)
Total synthesis of bengamide E and analogues by modification at C-2 and at terminal olefinic positions
Sarabia F and S'anchez-Ruiz A
The Journal of Organic Chemistry, 70(23), 9514-9520 (2005)
A diversity-oriented synthetic approach to bengamides
Sarabia F and S'anchez-Ruiz A
Tetrahedron Letters, 46(7), 1131-1135 (2005)

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