Carnosol - ≥98% , CAS No.5957-80-2

CAS: 5957-80-2 Cat. No.: C122021 Summenformel: C₂₀H₂₆O₄ Molekulargewicht: 330.42 EG-Nummer: 995-852-1

GRADE & PURITY ≥98%

Synonyms

.alpha.-Farnesene isomer | DTXSID80904451 | TRANS-.BETA.-FARNESENE | 2H-9,4a-(Epoxymethano)phenanthren-12-one, 1,3,4,9,10,10a-hexahydro-5,6-dihydroxy-1,1-dimethyl-7-(1-methylethyl)-, (4aR-(4aalpha,9alpha,10abeta))- | CARNOSOL [MI] | Picrosalvin | 2H-9,4A-

Storage

Lagerung bei -20°C

Shipped In

Eistruhe + Eispads

Übersicht

Carnosol ist ein natürlich vorkommendes phenolisches Diterpen, das im Rosmarin vorkommt. Es hat antioxidative, entzündungshemmende und Anti-Krebs-Aktivitäten.
Ist ein polyphenolisches Antioxidans, ein Hauptbestandteil der Pflanze Diego Rosmarin. Prävention und Qualität potenzielle Rolle bei der Alzheimer-Krankheit, Parkinson-Krankheit und anderen neurologischen Erkrankungen.

Specifications

Synonyme

.alpha.-Farnesene isomer | DTXSID80904451 | TRANS-.BETA.-FARNESENE | 2H-9,4a-(Epoxymethano)phenanthren-12-one, 1,3,4,9,10,10a-hexahydro-5,6-dihydroxy-1,1-dimethyl-7-(1-methylethyl)-, (4aR-(4aalpha,9alpha,10abeta))- | CARNOSOL [MI] | Picrosalvin | 2H-9,4A-

Spezifikationen & Reinheit

≥98%

Biochemische und physiologische Mechanismen

Phenolisches Diterpen mit antioxidativer und antikarzinogener Wirkung. antioxidationsmittel und Antikrebsmittel (IC 50-Werte liegen bei 9 und 82 μM für LPS-stimulierte NO-Produktion bzw. MCF-7-Zellen). Hemmt die Induktion von NFκB und COX-2. Wirkt auf PI

Storage

Lagerung bei -20°C

Verschickt in

Eistruhe + Eispads

Hinweis

Wenn möglich, sollten Sie die Lösungen noch am selben Tag zubereiten und verwenden. Wenn Sie jedoch Stammlösungen im Voraus herstellen müssen, empfehlen wir Ihnen, die Lösung als Aliquote in dicht verschlossenen Fläschchen bei -20 °C zu lagern. Diese sind in der Regel bis zu einem Monat haltbar. Vor der Verwendung und vor dem Öffnen des Fläschchens empfehlen wir, das Produkt mindestens 1 Stunde lang auf Raumtemperatur kommen zu lassen. Benötigen Sie weitere Ratschläge zur Löslichkeit, Verwendung und Handhabung? Besuchen Sie unsere Seite mit den häufig gestellten Fragen (FAQ) für weitere Informationen.

Reinheit

≥98%

Namen und Kennungen

• Pubchem Sid: 508817210
• Kanonisches Lächeln: CC(C)C1=C(C(=C2C(=C1)C3CC4C2(CCCC4(C)C)C(=O)O3)O)O
• IUPAC Name: (1R,8S,10S)-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
• InChIKey: XUSYGBPHQBWGAD-PJSUUKDQSA-N
• 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
• Isomere SMILES: CC(C)C1=C(C(=C2C(=C1)[C@@H]3C[C@@H]4[C@@]2(CCCC4(C)C)C(=O)O3)O)O
• WGK Deutschland: 3
• Molekulargewicht: 330.42
• Reaxy-Rn: 1296666
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1296666&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Klasse Prenol lipids
      • Subclass Terpene lactones

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Klasse: Prenol lipids
• Subclass: Terpene lactones
• Intermediate Tree Nodes: Not available
• Direct Parent: Diterpene lactones
• Alternative Parents: Diterpenoids Phenanthrenes and derivatives Tetralins 2-benzopyrans Delta valerolactones 1-hydroxy-4-unsubstituted benzenoids Oxanes Carboxylic acid esters Oxacyclic compounds Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Diterpene lactone - Diterpenoid - Phenanthrene - Benzopyran - Isochromane - 2-benzopyran - Tetralin - 1-hydroxy-4-unsubstituted benzenoid - Delta valerolactone - Delta_valerolactone - Benzenoid - Oxane - Carboxylic acid ester - Lactone - Carboxylic acid derivative - Oxacycle - Organoheterocyclic compound - Monocarboxylic acid or derivatives - Hydrocarbon derivative - Organic oxygen compound - Organic oxide - Organooxygen compound - Carbonyl group - Aromatic heteropolycyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.
• External Descriptors: Abietanes

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

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FDPS Tclin Farnesyl diphosphate synthase (1240 Activities)

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PNLIP Tclin Pancreatic lipase (198 Activities)

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CTSD Tchem Cathepsin D (3201 Activities)

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MCF7 (126967 Activities)

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A549 (127892 Activities)

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T47D (39041 Activities)

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HBL-100 (746 Activities)

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HEK293 (82097 Activities)

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HEp-2 (3859 Activities)

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WiDr (1835 Activities)

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HepG2 (196354 Activities)

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A2780 (11979 Activities)

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HeLa (62764 Activities)

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MDA-MB-231 (73002 Activities)

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SW1573 (1008 Activities)

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PTGES Prostaglandin E synthase (10 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Staphylococcus aureus (210822 Activities)

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Staphylococcus epidermidis (22802 Activities)

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Acinetobacter baumannii (41033 Activities)

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Escherichia coli (133304 Activities)

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Proteus mirabilis (3894 Activities)

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Salmonella (646 Activities)

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Bacillus subtilis (32866 Activities)

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Listeria monocytogenes (2626 Activities)

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Mycobacterium tuberculosis (203094 Activities)

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Enterococcus faecalis (29875 Activities)

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Bacillus cereus (7522 Activities)

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Mycolicibacterium smegmatis (8003 Activities)

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Candida albicans (78123 Activities)

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Vero (26788 Activities)

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Protease (18 Activities)

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Pectobacterium carotovorum (295 Activities)

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Wirkungsmechanismen

Chemische und physikalische Eigenschaften

• Molekulargewicht: 330.400 g/mol
• XLogP3: 4.400
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 330.183 Da
• Monoisotopic Mass: 330.183 Da
• Topological Polar Surface Area: 66.800 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 542.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Referenzen

1. Xie Lixia, Li Zhineng, Li Haitao, Sun Jiayu, Liu Xueying, Tang Jianxin, Lin Xizhu, Xu Laijun, Zhu Yuefang, Liu Zhi, Wang Tong.  (2022)  Fast Quantitative Determination of Principal Phenolic Anti-oxidants in Rosemary Using Ultrasound-Assisted Extraction and Chemometrics-Enhanced HPLC–DAD Method.  Food Analytical Methods,  16  (2): (386-400).  [PMID:] [10.1007/s12161-022-02421-0]

2. Xin-Yu Liu, Wen-Zhu Wang, Song-Po Yao, Xue-Ying Li, Rui-Min Han, Dangquan Zhang, Zhijun Zhao, Yapei Wang, Jian-Ping Zhang.  (2024)  Antioxidation Activity Enhancement by Intramolecular Hydrogen Bond and Non-Browning Mechanism of Active Ingredients in Rosemary: Carnosic Acid and Carnosol.  JOURNAL OF PHYSICAL CHEMISTRY B,      [PMID:39073136] [10.1021/acs.jpcb.4c02949]