ChemicalBook--->CAS DataBase List--->3705-26-8

3705-26-8

3705-26-8 Structure

3705-26-8 Structure
IdentificationBack Directory
[Name]

CYCLO(-PHE-PRO)
[CAS]

3705-26-8
[Synonyms]

Maculosine 2
CYCLO(-PHE-PRO)
Cyclo(Pro-Phe-)
Einecs 223-047-0
Cyclo(L-Phe-L-Pro-)
Cyclo(D-Pro-L-Phe-)
Cyclo(-Phe-Pro)≥ 99% (TLC)
CYCLO-L-PHENYLALANYL-L-PROLINE
Cyclo(L-prolyl-L-phenylalanyl)
Cyclo(L-phenylalanyl-L-prolyl)
L-Phenylalanyl-L-proline lactam
L-Prolyl-L-phenylalanine diketopiperazine
(3S,8AS)-3-benzylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione
(3S,8aα)-3β-Benzyloctahydropyrrolo[1,2-a]pyrazine-1,4-dione
(3S-trans)-3-benzylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione
Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(phenylmethyl)-, (3S,8aS)-
(3S,8aS)-3-Benzyl-6,7,8,8aα-tetrahydropyrrolo[1,2-a]pyrazine-1,4(2H,3H)-dione
(3S,8aS)-3β-Benzyl-6,7,8,8a-tetrahydropyrrolo[1,2-a]pyrazine-1,4(2H,3H)-dione
(3S)-2,3,6,7,8,8aβ-Hexahydro-3β-(phenylmethyl)pyrrolo[1,2-a]pyrazine-1,4-dione
[EINECS(EC#)]

223-047-0
[Molecular Formula]

C14H16N2O2
[MDL Number]

MFCD00038604
[MOL File]

3705-26-8.mol
[Molecular Weight]

244.29
Chemical PropertiesBack Directory
[Melting point ]

146-148 °C
[Boiling point ]

509.5±39.0 °C(Predicted)
[density ]

1.26±0.1 g/cm3(Predicted)
[storage temp. ]

-15°C
[solubility ]

Chloroform (Slightly), Ethanol (Slightly, Sonicated)
[form ]

Solid
[pka]

13.21±0.40(Predicted)
[color ]

White to Off-White
[Stability:]

Hygroscopic
[InChI]

1S/C14H16N2O2/c17-13-12-7-4-8-16(12)14(18)11(15-13)9-10-5-2-1-3-6-10/h1-3,5-6,11-12H,4,7-9H2,(H,15,17)/t11-,12-/m0/s1
[InChIKey]

QZBUWPVZSXDWSB-RYUDHWBXSA-N
[SMILES]

N21[C@@H](CCC2)C(=O)N[C@H](C1=O)Cc3ccccc3
Safety DataBack Directory
[WGK Germany ]

WGK 3
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[Chemical Properties]

White powder
[Uses]

Cyclo(L-Phe-L-Pro) is a diketopiperazine formed by the fusion of phenylalanine and proline, reported as a secondary metabolite of fungi and bacteria. In Pseudomonas aeruginosa, cyclo(L-Phe-L-Pro) is capable of activating N-acylhomoserine lactones (AHLs). Cyclo(L-Phe-L-Pro) is also capable of activating or antagonizing other LuxR-based quorum-sensing systems. While the mode of action of cyclo(L-Phe-L-Pro) is not known, its activity suggests the existence of cross talk among bacterial signalling systems.
[Uses]

Cyclo(L-prolyl-L-phenylalanyl) is a diketopiperazine derivative isolated from Bacillus thuringiensis and Bacillus endophyticus.
[Definition]

ChEBI: Cyclo(L-Phe-L-Pro) is an organic molecular entity. It has a role as a metabolite.
Spectrum DetailBack Directory
[Spectrum Detail]

CYCLO(-PHE-PRO)(3705-26-8)1HNMR
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