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139236-75-2 | 4a(2H)-Phenanthrenecarboxylic acid, 1,3,4,9,10,10a-hexahydro-5,6-dihydroxy-1,1-dimethyl-7-(1-methylethyl)-, (4aR,10aS)-rel-
CAS No: 139236-75-2 Catalog No: AG001AJC MDL No:
Product Description
Catalog Number:
AG001AJC
Chemical Name:
4a(2H)-Phenanthrenecarboxylic acid, 1,3,4,9,10,10a-hexahydro-5,6-dihydroxy-1,1-dimethyl-7-(1-methylethyl)-, (4aR,10aS)-rel-
CAS Number:
139236-75-2
Molecular Formula:
C20H28O4
Molecular Weight:
332.4339
IUPAC Name:
(4aR,10aS)-5,6-dihydroxy-1,1-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid
InChI:
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
InChI Key:
QRYRORQUOLYVBU-VBKZILBWSA-N
SMILES:
OC(=O)[C@@]12CCCC([C@@H]2CCc2c1c(O)c(c(c2)C(C)C)O)(C)C
EC Number:
609-253-7
UNII:
LI791SXT24
NSC Number:
694080
Properties
Complexity:
500
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
2
Defined Bond Stereocenter Count:
0
Exact Mass:
332.199g/mol
Formal Charge:
0
Heavy Atom Count:
24
Hydrogen Bond Acceptor Count:
4
Hydrogen Bond Donor Count:
3
Isotope Atom Count:
0
Molecular Weight:
332.44g/mol
Monoisotopic Mass:
332.199g/mol
Rotatable Bond Count:
2
Topological Polar Surface Area:
77.8A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
4.9
Literature
| Title | Journal |
|---|---|
| Carnosic acid induces apoptosis of hepatocellular carcinoma cells via ROS-mediated mitochondrial pathway. | Chemico-biological interactions 20171101 |
| Protective effect of carnosic acid against acrylamide-induced toxicity in RPE cells. | Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20171001 |
| Protective effect of carnosic acid against paraquat-induced redox impairment and mitochondrial dysfunction in SH-SY5Y cells: Role for PI3K/Akt/Nrf2 pathway. | Toxicology in vitro : an international journal published in association with BIBRA 20160401 |
| Carnosic acid biosynthesis elucidated by a synthetic biology platform. | Proceedings of the National Academy of Sciences of the United States of America 20160329 |
| Role for the PI3K/Akt/Nrf2 signaling pathway in the protective effects of carnosic acid against methylglyoxal-induced neurotoxicity in SH-SY5Y neuroblastoma cells. | Chemico-biological interactions 20151205 |
| Carnosic acid induces autophagic cell death through inhibition of the Akt/mTOR pathway in human hepatoma cells. | Journal of applied toxicology : JAT 20150501 |
| Carnosic acid protects against 6-hydroxydopamine-induced neurotoxicity in in vivo and in vitro model of Parkinson's disease: involvement of antioxidative enzymes induction. | Chemico-biological interactions 20150105 |
| Towards Elucidating Carnosic Acid Biosynthesis in Lamiaceae: Functional Characterization of the Three First Steps of the Pathway in Salvia fruticosa and Rosmarinus officinalis. | PloS one 20150101 |
| Induction of Pi form of glutathione S-transferase by carnosic acid is mediated through PI3K/Akt/NF-κB pathway and protects against neurotoxicity. | Chemical research in toxicology 20141117 |
| Sirtuin 1-mediated inhibition of p66shc expression alleviates liver ischemia/reperfusion injury. | Critical care medicine 20140501 |
| Small molecule activators of the Nrf2-HO-1 antioxidant axis modulate heme metabolism and inflammation in BV2 microglia cells. | Pharmacological research 20131001 |
| Acute and 30-day oral toxicity studies of administered carnosic acid. | Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20121201 |
| Synergism between carnosic acid and arsenic trioxide on induction of acute myeloid leukemia cell apoptosis is associated with modulation of PTEN/Akt signaling pathway. | Chinese journal of integrative medicine 20121201 |
| Carnosic acid inhibits the growth of ER-negative human breast cancer cells and synergizes with curcumin. | Fitoterapia 20121001 |
| The synergistic anti-inflammatory effects of lycopene, lutein, β-carotene, and carnosic acid combinations via redox-based inhibition of NF-κB signaling. | Free radical biology & medicine 20121001 |
| Effect of Rosemarinus officinalis L. on MMP-9, MCP-1 levels, and cell migration in RAW 264.7 and smooth muscle cells. | Journal of medicinal food 20121001 |
| Relevance of carnosic acid, carnosol, and rosmarinic acid concentrations in the in vitro antioxidant and antimicrobial activities of Rosmarinus officinalis (L.) methanolic extracts. | Journal of agricultural and food chemistry 20120926 |
| Carnosic acid prevents 6-hydroxydopamine-induced cell death in SH-SY5Y cells via mediation of glutathione synthesis. | Chemical research in toxicology 20120917 |
| Degradation study of carnosic acid, carnosol, rosmarinic acid, and rosemary extract (Rosmarinus officinalis L.) assessed using HPLC. | Journal of agricultural and food chemistry 20120912 |
| Extraction of betulin, trimyristin, eugenol and carnosic acid using water-organic solvent mixtures. | Molecules (Basel, Switzerland) 20120803 |
| Meat texture and antioxidant status are improved when carnosic acid is included in the diet of fattening lambs. | Meat science 20120801 |
| Carnosic acid (CA) prevents lipid accumulation in hepatocytes through the EGFR/MAPK pathway. | Journal of gastroenterology 20120701 |
| Carnosic acid modulates Akt/IKK/NF-κB signaling by PP2A and induces intrinsic and extrinsic pathway mediated apoptosis in human prostate carcinoma PC-3 cells. | Apoptosis : an international journal on programmed cell death 20120701 |
| Carnosol and carnosic acids from Salvia officinalis inhibit microsomal prostaglandin E2 synthase-1. | The Journal of pharmacology and experimental therapeutics 20120701 |
| In vitro hepatotoxicity and cytochrome P450 induction and inhibition characteristics of carnosic acid, a dietary supplement with antiadipogenic properties. | Drug metabolism and disposition: the biological fate of chemicals 20120701 |
| Concentration of antioxidant polyphenols from Thymus capitatus extracts by membrane process technology. | Journal of food science 20120601 |
| Effect of rosemary extract dose on lipid oxidation, colour stability and antioxidant concentrations, in reduced nitrite liver pâtés. | Meat science 20120401 |
| Carnosic acid inhibits the proliferation and migration capacity of human colorectal cancer cells. | Oncology reports 20120401 |
| Antiproliferation effect of Rosemary (Rosmarinus officinalis) on human ovarian cancer cells in vitro. | Phytomedicine : international journal of phytotherapy and phytopharmacology 20120315 |
| Carnosic acid dietary supplementation at 0.12% rates slows down meat discoloration in gluteus medius of fattening lambs. | Meat science 20120301 |
| An intrinsically labile α-helix abutting the BCL9-binding site of β-catenin is required for its inhibition by carnosic acid. | Nature communications 20120221 |
| Carnosic acid, a pro-electrophilic compound, inhibits LPS-induced activation of microglia. | Biochemical and biophysical research communications 20120203 |
| Antiangiogenic effect of carnosic acid and carnosol, neuroprotective compounds in rosemary leaves. | Bioscience, biotechnology, and biochemistry 20120101 |
| Syk/Src pathway-targeted inhibition of skin inflammatory responses by carnosic acid. | Mediators of inflammation 20120101 |
| Inhibition of gastric lipase as a mechanism for body weight and plasma lipids reduction in Zucker rats fed a rosemary extract rich in carnosic acid. | PloS one 20120101 |
| Ultrasound-assisted extraction of carnosic acid and rosmarinic acid using ionic liquid solution from Rosmarinus officinalis. | International journal of molecular sciences 20120101 |
| Effects of heat and ultraviolet radiation on the oxidative stability of pine nut oil supplemented with carnosic acid. | Journal of agricultural and food chemistry 20111228 |
| Carnosic acid, a rosemary phenolic compound, induces apoptosis through reactive oxygen species-mediated p38 activation in human neuroblastoma IMR-32 cells. | Neurochemical research 20111201 |
| Carnosic acid attenuates renal injury in an experimental model of rat cisplatin-induced nephrotoxicity. | Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20111201 |
| Application of ionic liquids based microwave-assisted simultaneous extraction of carnosic acid, rosmarinic acid and essential oil from Rosmarinus officinalis. | Journal of chromatography. A 20111125 |
| Low-molecular-weight compounds having neurotrophic activity in cultured PC12 cells and neurons. | Journal of biochemistry 20111101 |
| Carnosic acid-rich rosemary (Rosmarinus officinalis L.) leaf extract limits weight gain and improves cholesterol levels and glycaemia in mice on a high-fat diet. | The British journal of nutrition 20111001 |
| Kinetin applications alleviate salt stress and improve the antioxidant composition of leaf extracts in Salvia officinalis. | Plant physiology and biochemistry : PPB 20111001 |
| Upregulation of endogenous neurotrophin levels in the brain by intranasal administration of carnosic acid. | Journal of pharmaceutical sciences 20110801 |
| Nrf2 regulates NGF mRNA induction by carnosic acid in T98G glioblastoma cells and normal human astrocytes. | Journal of biochemistry 20110801 |
| Chemical genoprotection: reducing biological damage to as low as reasonably achievable levels. | Dento maxillo facial radiology 20110701 |
| Gastroprotective effect and cytotoxicity of carnosic acid derivatives. | Planta medica 20110601 |
| Absorption, distribution and elimination of carnosic acid, a natural antioxidant from Rosmarinus officinalis, in rats. | Plant foods for human nutrition (Dordrecht, Netherlands) 20110601 |
| Anti-inflammatory effects of supercritical carbon dioxide extract and its isolated carnosic acid from Rosmarinus officinalis leaves. | Journal of agricultural and food chemistry 20110427 |
| Edaravone and carnosic acid synergistically enhance the expression of nerve growth factor in human astrocytes under hypoxia/reoxygenation. | Neuroscience research 20110401 |
| Chemical stabilization of oils rich in long-chain polyunsaturated fatty acids during storage. | Food science and technology international = Ciencia y tecnologia de los alimentos internacional 20110401 |
| Rosemary extracts improve flow-mediated dilatation of the brachial artery and plasma PAI-1 activity in healthy young volunteers. | Phytotherapy research : PTR 20110301 |
| The Nrf2 transcription factor is a positive regulator of myeloid differentiation of acute myeloid leukemia cells. | Cancer biology & therapy 20110201 |
| Development of a high-throughput screening assay for cytoprotective agents in rotenone-induced cell death. | Analytical biochemistry 20101215 |
| Carnosic acid: a potent chemopreventive agent against oral carcinogenesis. | Chemico-biological interactions 20101205 |
| Activation of the nuclear receptor PPARγ by metabolites isolated from sage (Salvia officinalis L.). | Journal of ethnopharmacology 20101028 |
| Importance of extract standardization and in vitro/ex vivo assay selection for the evaluation of antioxidant activity of botanicals: a case study on three Rosmarinus officinalis L. extracts. | Journal of medicinal food 20101001 |
| Rosmarinus officinalis polyphenols activate cholinergic activities in PC12 cells through phosphorylation of ERK1/2. | Journal of ethnopharmacology 20100915 |
| Tumor suppressor p53 status does not determine the differentiation-associated G₁ cell cycle arrest induced in leukemia cells by 1,25-dihydroxyvitamin D₃ and antioxidants. | Cancer biology & therapy 20100815 |
| Distinct combinatorial effects of the plant polyphenols curcumin, carnosic acid, and silibinin on proliferation and apoptosis in acute myeloid leukemia cells. | Nutrition and cancer 20100801 |
| Antimicrobial activity of Rosmarinus officinalis against oral pathogens: relevance of carnosic acid and carnosol. | Chemistry & biodiversity 20100701 |
| Inhibitory effects of rosemary extracts, carnosic acid and rosmarinic acid on the growth of various human cancer cell lines. | Plant foods for human nutrition (Dordrecht, Netherlands) 20100601 |
| Activated glutathione metabolism participates in protective effects of carnosic acid against oxidative stress in neuronal HT22 cells. | Planta medica 20100501 |
| Gastroprotective effect of carnosic acid gamma-lactone derivatives. | Journal of natural products 20100423 |
| Role of Nrf2 and p62/ZIP in the neurite outgrowth by carnosic acid in PC12h cells. | Journal of biochemistry 20100101 |
| Syntheses of carnosic acid and carnosol, anti-oxidants in Rosemary, from pisiferic acid, the major constituent of Sawara. | Chemical & pharmaceutical bulletin 20100101 |
| Influence of ionic interactions on essential oil and phenolic diterpene composition of Dalmatian sage (Salvia officinalis L.). | Plant physiology and biochemistry : PPB 20100101 |
| Novel screening method for potential skin-whitening compounds by a luciferase reporter assay. | Bioscience, biotechnology, and biochemistry 20100101 |
| Anti-clastogenic potential of carnosic acid against 7,12-dimethylbenz(a)anthracene (DMBA)-induced clastogenesis. | Pharmacological reports : PR 20100101 |
| Inhibition of the dimerization and active site of HIV-1 protease by secondary metabolites from the Vietnamese mushroom Ganoderma colossum. | Journal of natural products 20091101 |
| c-Jun N-terminal kinase 2 (JNK2) antagonizes the signaling of differentiation by JNK1 in human myeloid leukemia cells resistant to vitamin D. | Leukemia research 20091001 |
| High-performance liquid chromatography method for determination of carnosic acid in rat plasma and its application to pharmacokinetic study. | Biomedical chromatography : BMC 20090701 |
| Carnosic acid and carnosol inhibit adipocyte differentiation in mouse 3T3-L1 cells through induction of phase2 enzymes and activation of glutathione metabolism. | Biochemical and biophysical research communications 20090508 |
| Carnosic acid reduces cytokine-induced adhesion molecules expression and monocyte adhesion to endothelial cells. | European journal of nutrition 20090301 |
| [Determination of carnosic acid in rat stomach and intestine by high performance liquid chromatography method]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20090301 |
| Simple ortho- and para-hydroquinones as compounds neuroprotective against oxidative stress in a manner associated with specific transcriptional activation. | Biochemical and biophysical research communications 20090206 |
| The enhancement and scale up of the extraction of anti-oxidants from Rosmarinus officinalis using ultrasound. | Ultrasonics sonochemistry 20090201 |
| Reversion of P-glycoprotein-mediated multidrug resistance in human leukemic cell line by carnosic acid. | The Chinese journal of physiology 20081231 |
| Piperine analogs as potent Staphylococcus aureus NorA efflux pump inhibitors. | Bioorganic & medicinal chemistry 20081115 |
| Carnosic acid prevents the migration of human aortic smooth muscle cells by inhibiting the activation and expression of matrix metalloproteinase-9. | The British journal of nutrition 20081001 |
| Synergistic antileukemic activity of carnosic acid-rich rosemary extract and the 19-nor Gemini vitamin D analogue in a mouse model of systemic acute myeloid leukemia. | Oncology 20081001 |
| Beneficial effects of carnosic acid on dieldrin-induced dopaminergic neuronal cell death. | Neuroreport 20080827 |
| Carnosic acid and carnosol potently inhibit human 5-lipoxygenase and suppress pro-inflammatory responses of stimulated human polymorphonuclear leukocytes. | Biochemical pharmacology 20080701 |
| Citral derived amides as potent bacterial NorA efflux pump inhibitors. | Bioorganic & medicinal chemistry 20080701 |
| Carnosic acid protects neuronal HT22 Cells through activation of the antioxidant-responsive element in free carboxylic acid- and catechol hydroxyl moieties-dependent manners. | Neuroscience letters 20080404 |
| Carnosic acid, a catechol-type electrophilic compound, protects neurons both in vitro and in vivo through activation of the Keap1/Nrf2 pathway via S-alkylation of targeted cysteines on Keap1. | Journal of neurochemistry 20080201 |
| [Enhancement of differentiation induction of HL-60 cells by 1,25-dihydroxyvitamin D3 in combination with carnosic acid]. | Zhongguo dang dai er ke za zhi = Chinese journal of contemporary pediatrics 20080201 |
| Augmentation by carnosic acid of apoptosis in human leukaemia cells induced by arsenic trioxide via upregulation of the tumour suppressor PTEN. | The Journal of international medical research 20080101 |
| Direct determination of carnosic acid in a new active packaging based on natural extract of rosemary. | Analytical and bioanalytical chemistry 20071101 |
| Enhanced carnosic acid levels in two rosemary accessions exposed to cold stress conditions. | Journal of agricultural and food chemistry 20071003 |
| Characterization of two unknown compounds in methanol extracts of rosemary oil. | Journal of agricultural and food chemistry 20070905 |
| The biology and chemistry of hyperlipidemia. | Bioorganic & medicinal chemistry 20070715 |
| Potential of rosemary (Rosemarinus officinalis L.) diterpenes in preventing lipid hydroperoxide-mediated oxidative stress in Caco-2 cells. | Journal of agricultural and food chemistry 20070221 |
| Potentiation of antimicrobial activity of aminoglycosides by carnosol from Salvia officinalis. | Biological & pharmaceutical bulletin 20070201 |
| Antiplatelet activity of carnosic acid, a phenolic diterpene from Rosmarinus officinalis. | Planta medica 20070201 |
| Carnosic acid from rosemary extracts: a potential chemoprotective agent against aflatoxin B1. An in vitro study. | Journal of applied toxicology : JAT 20070101 |
| Isolation of functional ingredients from rosemary by preparative-supercritical fluid chromatography (Prep-SFC). | Journal of pharmaceutical and biomedical analysis 20060828 |
| Carnosic acid and carnosol, phenolic diterpene compounds of the labiate herbs rosemary and sage, are activators of the human peroxisome proliferator-activated receptor gamma. | Planta medica 20060801 |
| Cooperative antitumor effects of vitamin D3 derivatives and rosemary preparations in a mouse model of myeloid leukemia. | International journal of cancer 20060615 |
| Induction of G2/M phase cell cycle arrest by carnosol and carnosic acid is associated with alteration of cyclin A and cyclin B1 levels. | Cancer letters 20060608 |
| Radioprotective-antimutagenic effects of rosemary phenolics against chromosomal damage induced in human lymphocytes by gamma-rays. | Journal of agricultural and food chemistry 20060322 |
| Antioxidant and antimicrobial activities of rosemary extracts linked to their polyphenol composition. | Free radical research 20060201 |
| LC-NMR coupling technology: recent advancements and applications in natural products analysis. | Magnetic resonance in chemistry : MRC 20050901 |
| Pressurized liquid extraction-capillary electrophoresis-mass spectrometry for the analysis of polar antioxidants in rosemary extracts. | Journal of chromatography. A 20050819 |
| seco-Hinokiol, a new abietane diterpenoid from Rosmarinus officinalis. | Journal of natural products 20050101 |
| Antibacterial and resistance modifying activity of Rosmarinus officinalis. | Phytochemistry 20041201 |
| Separation of rosemary antioxidant compounds by supercritical fluid chromatography on coated packed capillary columns. | Journal of chromatography. A 20041119 |
| Relevance of carnosic acid concentrations to the selection of rosemary, Rosmarinus officinalis (L.), accessions for optimization of antioxidant yield. | Journal of agricultural and food chemistry 20041006 |
| Potential for the use of ultrasound in the extraction of antioxidants from Rosmarinus officinalis for the food and pharmaceutical industry. | Ultrasonics sonochemistry 20040501 |
| Carnosic acid, a new class of lipid absorption inhibitor from sage. | Bioorganic & medicinal chemistry letters 20040419 |
| Calculation of the molar absorptivity of polyphenols by using liquid chromatography with diode array detection: the case of carnosic acid. | Journal of chromatography. A 20040116 |
| Antioxidant activity of organic extracts from aqueous infusions of sage. | Journal of agricultural and food chemistry 20031105 |
| Carnosic acid, a component of rosemary (Rosmarinus officinalis L.), promotes synthesis of nerve growth factor in T98G human glioblastoma cells. | Biological & pharmaceutical bulletin 20031101 |
| Phenolic diterpenes, flavones, and rosmarinic acid distribution during the development of leaves, flowers, stems, and roots of Rosmarinus officinalis. Antioxidant activity. | Journal of agricultural and food chemistry 20030716 |
| Catechols from abietic acid synthesis and evaluation as bioactive compounds. | Bioorganic & medicinal chemistry 20030417 |
| Drought-induced changes in the redox state of alpha-tocopherol, ascorbate, and the diterpene carnosic acid in chloroplasts of Labiatae species differing in carnosic acid contents. | Plant physiology 20030401 |
| Carnosic acid potentiates the antioxidant and prodifferentiation effects of 1alpha,25-dihydroxyvitamin D3 in leukemia cells but does not promote elevation of basal levels of intracellular calcium. | Cancer research 20030315 |
| Rapid quantitative enrichment of carnosic acid from rosemary (Rosmarinus officinalis L.) by isoelectric focused adsorptive bubble chromatography. | Journal of agricultural and food chemistry 20030226 |
| Subcritical water extraction of antioxidant compounds from rosemary plants. | Journal of agricultural and food chemistry 20030115 |
| Recovery mechanism of the antioxidant activity from carnosic acid quinone, an oxidized sage and rosemary antioxidant. | Journal of agricultural and food chemistry 20021009 |
| Oxidation, reduction, and methylation of carnosic acid by Nocardia. | Journal of natural products 20020901 |
| Antioxidant capacity of abietanes from Sphacele salviae. | Natural product letters 20020801 |
| Semisynthesis of rosmanol and its derivatives. Easy access to abietatriene diterpenes isolated from the genus Salvia with biological activities. | Journal of natural products 20020701 |
| Photoprotective potential of lycopene, beta-carotene, vitamin E, vitamin C and carnosic acid in UVA-irradiated human skin fibroblasts. | Free radical biology & medicine 20020615 |
| Antioxidant mechanism of carnosic acid: structural identification of two oxidation products. | Journal of agricultural and food chemistry 20011101 |
| Carnosic acid and promotion of monocytic differentiation of HL60-G cells initiated by other agents. | Journal of the National Cancer Institute 20010815 |
| Subcellular compartmentation of the diterpene carnosic acid and its derivatives in the leaves of rosemary. | Plant physiology 20010201 |
| Carnosic acid inhibits proliferation and augments differentiation of human leukemic cells induced by 1,25-dihydroxyvitamin D3 and retinoic acid. | Nutrition and cancer 20010101 |
| An evaluation of the antioxidant and antiviral action of extracts of rosemary and Provençal herbs. | Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 19960501 |
| Inhibitory effect of carnosic acid on HIV-1 protease in cell-free assays [corrected]. | Journal of natural products 19930801 |
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