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21612

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:
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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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 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)
Total synthesis of bengamide E
Liu W, et al.
Tetrahedron Letters, 43(8), 1373-1375 (2002)
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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