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Citato in 5 pubblicazioni peer-reviewed su cromatografia, sintesi organica e reazioni di accoppiamento incrociato.

Panoramica

Carnosic acid is a diterpenoid that acts as an effective lipid peroxidation inhibitor in liposomal and microsomal environments, with antioxidant properties. Carnosic acid has been reported to scavenge peroxyl radicals, H2O2, reduce cytochrome C, and act more potently than Propyl gallate.Studies indicate that Carnosic acid protects red cells from oxidative hemolysis and in the xanthine/xanthine oxidase system inhibits superoxide anion production. In addition, data suggests that Carnosic acid activates PPARγ (peroxisome proliferator activated receptor γ).
An antioxidant, lipid peroxidation inhibitor, and PPARγ activator

Specifiche

Sinonimi

Specifiche e purezza

10mM in DMSO

Meccanismi biochimici e fisiologici

Found in Rosmarinus officinalis . Displays antioxidative, anticancer, antiangiogenic, anti-inflammatory, and hepatoprotective and neuroprotective effects.

Condizioni di conservazione di stoccaggio

Store at -80°C

Spedito in

Dry ice packs + Cold packs

Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.

Tipo di azione

INHIBITOR

Nomi e identificatori

Pubchem Sid

528776727

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/528776727

Sorrisi canonici

CC(C)C1=C(C(=C2C(=C1)CCC3C2(CCCC3(C)C)C(=O)O)O)O

IUPAC Name

(4aR,10aS)-5,6-dihydroxy-1,1-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid

InChIKey

QRYRORQUOLYVBU-VBKZILBWSA-N

INCHI

1S/C20H28O4/c1-11(2)13-10-12-6-7-14-19(3,4)8-5-9-20(14,18(23)24)15(12)17(22)16(13)21/h10-11,14,21-22H,5-9H2,1-4H3,(H,23,24)/t14-,20+/m0/s1

Isomeri SMILES

CC(C)C1=C(C(=C2C(=C1)CC[C@@H]3[C@@]2(CCCC3(C)C)C(=O)O)O)O

WGK Germania

Peso molecolare

332.43

Beilstein

2707918

Reaxy-Rn

2774884

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2774884&ln=

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Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
- Superclass Lipids and lipid-like molecules
  - Classe Prenol lipids
    - Subclass Diterpenoids

Kingdom	Organic compounds
Superclass	Lipids and lipid-like molecules
Classe	Prenol lipids
Subclass	Diterpenoids
Intermediate Tree Nodes	Not available
Direct Parent	Diterpenoids
Alternative Parents	Hydrophenanthrenes Naphthalenecarboxylic acids Tetralins 1-hydroxy-4-unsubstituted benzenoids Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
Molecular Framework	Aromatic homopolycyclic compounds
Substituents	Abietane diterpenoid - Diterpenoid - Hydrophenanthrene - Phenanthrene - 1-naphthalenecarboxylic acid - 1-naphthalenecarboxylic acid or derivatives - Tetralin - 1-hydroxy-4-unsubstituted benzenoid - Benzenoid - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Organic oxide - Organic oxygen compound - Aromatic homopolycyclic compound
Descrizione	This compound belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.
External Descriptors	monocarboxylic acid - catechols - abietane diterpenoid - carbotricyclic compound
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

Struttura 3D

Obiettivi associati (umani)

VDR Tclin Vitamin D receptor (26531 Activities)

Discover Target: VDR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

FDPS Tclin Farnesyl diphosphate synthase (1240 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PNLIP Tclin Pancreatic lipase (198 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CTSD Tchem Cathepsin D (3201 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GGPS1 Tchem Geranylgeranyl pyrophosphate synthetase (715 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2C8 Tchem Cytochrome P450 2C8 (1492 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALOX15B Tchem Arachidonate 15-lipoxygenase, type II (7244 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALOX12 Tchem Arachidonate 12-lipoxygenase (3262 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GSTO1 Tchem Glutathione transferase omega 1 (164 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2E1 Tchem Cytochrome P450 2E1 (2174 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2B6 Tchem Cytochrome P450 2B6 (1338 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ACHN (49357 Activities)

Sensibilità	light sensitive
Rotazione specifica [α]	184 ° (C=1, MeOH)
Punto di fusione (°C)	190°C
Peso molecolare	332.400 g/mol
XLogP3	4.900
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	2
Exact Mass	332.199 Da
Monoisotopic Mass	332.199 Da
Topological Polar Surface Area	77.800 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	500.000
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
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

Carnosic acid - 10mM in DMSO , CAS No.3650-09-7

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