(1R)-3,4-Dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-one
Grundinformationen
- CAS
5957-80-2- Standard-SMILES
CC(C)c1cc2c(c(O)c1O)C13CCCC(C)(C)C1CC2OC3=O- InChIKey
XUSYGBPHQBWGAD-UHFFFAOYSA-N- Summenformel
- C20H26O4
- Durchschnittliche Molmasse
- 330,4 g/mol
- Monoisotopische Masse
- 330,18310931
Überblick
(1R)-3,4-Dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-one has been reported in Salvia officinalis, Salvia chionopeplica, and other organisms with data available.
Namen und Bezeichner
- Bevorzugter Name
- (1R)-3,4-Dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-one
- IUPAC
- 3,4-dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-one
- Englischer Name
- CARNOSOL
- Summenformel
- C20H26O4
- Molmasse
- 330.42
Namen und Synonyme
(1R)-3,4-Dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-oneCarnosol [M+H]+MEGxp0_001119orb1221988SCHEMBL18290355XUSYGBPHQBWGAD-UHFFFAOYSA-NHMS3649B031,3,4,9,10,10aS-Hexahydro-5,6-dihydroxy-1,1-dimethyl-7-isopropyl-2H-9S,4aR-(epoxymethano)phenanthren-12-oneNSC39143s9127EBC-627307SMP2_000248
Weitere Namen anzeigen
carnolCARNOSOLBCL6-IN-13D-α-AlanineCarnosol-RMCARNOSOL(RG)CARNOSOL USP/EP/BPCarnosol (Standard)Carnosol, 10 mM in DMSOCarnosol(P)(Request Quote)
NCGC00344316-023,4-Dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-oneSR-01000946633SR-01000946633-1(1R,8S,10S)-3,4-dihydroxy-11,11-dimethyl-5-propan-2-yl-16-oxatetracyclo[6.6.2.0^{1,10.0^{2,7]hexadeca-2,4,6-trien-15-one1,3,4,9,10,10aS-hexahydro-5,6-dihydroxy-1,1-dimethyl-7-isopropyl-2H-9S,4aR-(epoxymethano)phenanthren-12-one (Musechem)3,4-dihydroxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[6.6.2.0^{1,10}.0^{2,7}]hexadeca-2,4,6-trien-15-one3,4-dihydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.01,10.02,7]hexadeca-2,4,6-trien-15-one
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 4,4
- Polarare Oberfläche (TPSA)
- 66,8 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 24
- Formalladung
- 0
- Komplexität
- 542
Physikochemische Eigenschaften
- Schmelzpunkt
- 240 · 240~242℃
- Siedepunkt
- 524.8 · 524.8±50.0 °C(Predicted)
- Dichte
- 1.26 · 1.26±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Sealed in dry,Store in freezer, under -20°C
- Löslichkeit
- 66 · DMSO:66.0(Max Conc. mg/mL);199.74(Max Conc. mM)
- Aggregatzustand
- Solid
- pka
- 8.91 · 8.91±0.40(Predicted)
- Farbe
- White
- Biologische Quelle
- Rosemarinus officinalis L. leaves
- Major Application
- food and beverages
- InChI
- InChI=1S/C20H26O4/c1-10(2)11-8-12-13-9-14-19(3,4)6-5-7-20(14,18(23)24-13)15(12)17(22)16(11)21/h8,10,13-14,21-22H,5-7,9H2,1-4H3/t13-,14-,20+/m0/s1
- InChIKey
- XUSYGBPHQBWGAD-PJSUUKDQSA-N
- SMILES
- C1(C)(C)[C@@]2([H])[C@]3(C(=O)O[C@@]([H])(C2)C2=C3C(O)=C(O)C(C(C)C)=C2)CCC1
- LogP
- 2.832 · 2.832 (est)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- wgk
- 3
- hs_code
- 29322090
- safety_code
- 24/25
- Speicherklasse
- 11 - Combustible Solids
- Giftige Stoffe Daten
- 5957-80-2(Hazardous Substances Data)
- Hazard Classifications
- Skin Sens. 1
Chemie und Industrie
Anwendungen
BeschreibungCarnosol is a phenol that has been found in rosemary (R. officinalis) and has diverse biological activities. It decreases nitric oxide (NO) production in mouse peritoneal exudate macrophages when used at concentrations ranging from 6 to 25 μM. Carnosol scavenges peroxyl and hydroxyl radicals and inhibits lipid peroxidation in cell-free assays. It inhibits 5-lipoxygenase (5-LO; IC50 = 0.1 μM for the recombinant human enzyme) and the synthesis of leukotrienes in human polymorphonuclear leukocytes (PMNs; IC50 = 7 μM). In vivo, carnosol (200 mg/kg) reduces mammary DNA adduct formation and tumorigenesis in a rat model of DMBA-induced mammary tumorigenesis.
VerwendenCarnosol is a phytopolyphenol found in Rosemary that functions as an antioxidant, antimicrobial, & anticarcinogen.
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