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carnosol

Chemical Structure

General Material Information

Preferred name carnosol
Trivial Name Carnosol
Short Description (4aR- (4aalpha, 9alpha, 10abeta))- 1,3,4,9,10,10a-hexahydro-5,6-dihydroxy-1,1-dimethyl-7-(1-methylethyl)-2H-9,4a-(epoxymethano)phenanthren-12-one
Formula C20 H26 O4
CAS Number 5957-80-2
FDA UNII 483O455CKD
MDL MFCD02752467
xLogP3-AA 4.40 (est)
NMR Predictor External link
Applications
  • natural substances and extractives
Synonyms
  • (4aR- (4aalpha, 9alpha, 10abeta))- 1,3,4,9,10,10a- hexahydro-5,6-dihydroxy-1,1-dimethyl-7-(1-methylethyl)-2H-9,4a-(epoxymethano)phenanthren-12-one
  • 2H-9,4a-(Epoxymethano)phenanthren-12-one, 1,3,4,9,10,10a-hexahydro-5,6-dihydroxy-1,1-dimethyl-7-(1-methylethyl)-, (4aR,9S,10aS)-
  • Picrosalvin
  • Podocarpa-8,11,13-trien-17-oic acid, 7β,11,12-trihydroxy-13-isopropyl-, 17,7-lactone
  • 2H-9,4a-(Epoxymethano)phenanthren-12-one, 1,3,4,9,10,10a-hexahydro-5,6-dihydroxy-1,1-dimethyl-7-(1-methylethyl)-, [4aR-(4aα,9α,10aβ)]-
  • (4aR,9S,10aS)-1,3,4,9,10,10a-Hexahydro-5,6-dihydroxy-1,1-dimethyl-7-(1-methylethyl)-2H-9,4a-(epoxymethano)phenanthren-12-one
  • NSC 39143
  • (4AR,10aS)-5,6-Dihydroxy-7-isopropyl-1,1-dimethyl-1,3,4,9,10,10a-hexahydro-2H-9,4a-(epoxymethano)phenanthren-12-one

Occurrences

rosemary leaf
rosemary plant
rosemary shoot
sage leaf
sage plant
sage sap
sage shoot

Potential Uses

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Literature & References

NIST Chemistry WebBook:Search Inchi
Pubchem (cid):65158
Pubchem (sid):135023128
Publications by PubMed
Carnosol: a phenolic diterpene with cancer chemopreventive potential.
Carnosol Induces ROS-Mediated Beclin1-Independent Autophagy and Apoptosis in Triple Negative Breast Cancer.
Antiulcer activity of the ethanolic extract and ethyl acetate fraction of the leaves of Markhamia tomentosa in rats.
Comprehensive foodomics study on the mechanisms operating at various molecular levels in cancer cells in response to individual rosemary polyphenols.
Improving the sensory and oxidative stability of cooked and chill-stored lamb using dietary rosemary diterpenes.
Evaluation of anti-cancer and immunomodulatory effects of carnosol in a Balb/c WEHI-164 fibrosarcoma model.
Expression of microRNA-15b and the glycosyltransferase GCNT3 correlates with antitumor efficacy of Rosemary diterpenes in colon and pancreatic cancer.
Bioactive compounds from culinary herbs inhibit a molecular target for type 2 diabetes management, dipeptidyl peptidase IV.
Antitumor activity of the dietary diterpene carnosol against a panel of human cancer cell lines.
Characterization of two genes for the biosynthesis of abietane-type diterpenes in rosemary (Rosmarinus officinalis) glandular trichomes.
Hydroalcoholic extract of Rosemary (Rosmarinus officinalis L.) and its constituent carnosol inhibit formalin-induced pain and inflammation in mice.
Carnosol induces apoptosis through generation of ROS and inactivation of STAT3 signaling in human colon cancer HCT116 cells.
Relevance of the carnosic acid/carnosol ratio for the level of rosemary diterpene transfer and for improving lamb meat antioxidant status.
Shelf life of meat from lambs given essential oil-free rosemary extract containing carnosic acid plus carnosol at 200 or 400 mg kg⁻¹.
Molecular approaches toward targeted cancer prevention with some food plants and their products: inflammatory and other signal pathways.
Carnosol, rosemary ingredient, induces apoptosis in adult T-cell leukemia/lymphoma cells via glutathione depletion: proteomic approach using fluorescent two-dimensional differential gel electrophoresis.
Carnosol inhibits cell adhesion molecules and chemokine expression by tumor necrosis factor-α in human umbilical vein endothelial cells through the nuclear factor-κB and mitogen-activated protein kinase pathways.
Screening of natural compounds as activators of the keap1-nrf2 pathway.
Systemic administration of Rosmarinus officinalis attenuates the inflammatory response induced by carrageenan in the mouse model of pleurisy.
Reprint of: Nrf2/ARE-mediated antioxidant actions of pro-electrophilic drugs.
Graphene-epoxy composite electrode fabricated by in situ polycondensation for enhanced amperometric detection in capillary electrophoresis.
Rosmarinus officinalis L. leaf extract improves memory impairment and affects acetylcholinesterase and butyrylcholinesterase activities in rat brain.
Calcium and α-tocopherol suppress cured-meat promotion of chemically induced colon carcinogenesis in rats and reduce associated biomarkers in human volunteers.
Small molecule activators of the Nrf2-HO-1 antioxidant axis modulate heme metabolism and inflammation in BV2 microglia cells.
Nrf2/ARE-mediated antioxidant actions of pro-electrophilic drugs.
Rosmarinus officinalis L. as cause of contact dermatitis.
Bioavailability of the major bioactive diterpenoids in a rosemary extract: metabolic profile in the intestine, liver, plasma, and brain of Zucker rats.
CYP1A1 regulates breast cancer proliferation and survival.
Polyphenols from the Mediterranean herb rosemary (Rosmarinus officinalis) for prostate cancer.
Rosmarinus officinalis extract suppresses Propionibacterium acnes-induced inflammatory responses.
Structure activity relationship of phenolic diterpenes from Salvia officinalis as activators of the nuclear factor E2-related factor 2 pathway.
Carnosol, radiation and melanoma: a translational possibility.
Supercritical carbon dioxide extraction of antioxidants from rosemary (Rosmarinus officinalis) leaves for use in edible vegetable oils.
Antidepressant-like effects of fractions, essential oil, carnosol and betulinic acid isolated from Rosmarinus officinalis L.
Effect of Rosemarinus officinalis L. on MMP-9, MCP-1 levels, and cell migration in RAW 264.7 and smooth muscle cells.
The antioxidant effect of carnosol in bovine aortic endothelial cells is mainly mediated via estrogen receptor α pathway.
Relevance of carnosic acid, carnosol, and rosmarinic acid concentrations in the in vitro antioxidant and antimicrobial activities of Rosmarinus officinalis (L.) methanolic extracts.
Degradation study of carnosic acid, carnosol, rosmarinic acid, and rosemary extract (Rosmarinus officinalis L.) assessed using HPLC.
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.
Carnosol and carnosic acids from Salvia officinalis inhibit microsomal prostaglandin E2 synthase-1.
Holistic Control of Herbal Teas and Tinctures Based on Sage (Salvia officinalis L.) for Compounds with Beneficial and Adverse Effects using NMR Spectroscopy.
Carnosol, a constituent of Zyflamend, inhibits aryl hydrocarbon receptor-mediated activation of CYP1A1 and CYP1B1 transcription and mutagenesis.
Antiproliferation effect of Rosemary (Rosmarinus officinalis) on human ovarian cancer cells in vitro.
Antiangiogenic effect of carnosic acid and carnosol, neuroprotective compounds in rosemary leaves.
Anti-angiogenic properties of carnosol and carnosic acid, two major dietary compounds from rosemary.
Optimization of ultrasound assisted extraction of antioxidant compounds from marjoram (Origanum majorana L.) using response surface methodology.
Antinociceptive and anti-inflammatory potential of extract and isolated compounds from the leaves of Salvia officinalis in mice.
Carnosic acid induces the NAD(P)H: quinone oxidoreductase 1 expression in rat clone 9 cells through the p38/nuclear factor erythroid-2 related factor 2 pathway.
[Dietetic factors associated with prostate cancer: protective effects of Mediterranean diet].
Rosemary and cancer prevention: preclinical perspectives.
Kinetin applications alleviate salt stress and improve the antioxidant composition of leaf extracts in Salvia officinalis.
Comparison of different extraction procedures for the comprehensive characterization of bioactive phenolic compounds in Rosmarinus officinalis by reversed-phase high-performance liquid chromatography with diode array detection coupled to electrospray time-of-flight mass spectrometry.
Structure and function of the oxidation products of polyphenols and identification of potent lipoxygenase inhibitors from Fe-catalyzed oxidation of resveratrol.
Storage method, drying processes and extraction procedures strongly affect the phenolic fraction of rosemary leaves: an HPLC/DAD/MS study.
Chemopreventive effects of dietary phytochemicals against cancer invasion and metastasis: phenolic acids, monophenol, polyphenol, and their derivatives.
Carnosol: a promising anti-cancer and anti-inflammatory agent.
Anti-inflammatory effects of supercritical carbon dioxide extract and its isolated carnosic acid from Rosmarinus officinalis leaves.
ent-Rosane and abietane diterpenoids as cancer chemopreventive agents.
Upregulation of NF-E2-related factor-2-dependent glutathione by carnosol provokes a cytoprotective response and enhances cell survival.
Suppression of COX-2, IL-1β and TNF-α expression and leukocyte infiltration in inflamed skin by bioactive compounds from Rosmarinus officinalis L.
Rosmanol potently induces apoptosis through both the mitochondrial apoptotic pathway and death receptor pathway in human colon adenocarcinoma COLO 205 cells.
Novel screening method for potential skin-whitening compounds by a luciferase reporter assay.
Coffee, broccoli and spices are strong inducers of electrophile response element-dependent transcription in vitro and in vivo - studies in electrophile response element transgenic mice.
Protective effect of carnosol on lung injury induced by intestinal ischemia/reperfusion.
Disruption of androgen and estrogen receptor activity in prostate cancer by a novel dietary diterpene carnosol: implications for chemoprevention.
Rosemary extracts improve flow-mediated dilatation of the brachial artery and plasma PAI-1 activity in healthy young volunteers.
Antimicrobial activity of Rosmarinus officinalis against oral pathogens: relevance of carnosic acid and carnosol.
Introduction of distillate rosemary leaves into the diet of the Murciano-Granadina goat: transfer of polyphenolic compounds to goats' milk and the plasma of suckling goat kids.
Inhibition of heterocyclic amine formation in beef patties by ethanolic extracts of rosemary.
Flavonoids and phenolic compounds from Rosmarinus officinalis.
Investigation of antioxidant and rosmarinic acid variation in the sage collection of the genebank in Gatersleben.
Dual mechanisms of NF-kappaB inhibition in carnosol-treated endothelial cells.
The plant phenolic diterpene carnosol suppresses sodium nitroprusside-induced toxicity in c6 glial cells.
Syntheses of carnosic acid and carnosol, anti-oxidants in Rosemary, from pisiferic acid, the major constituent of Sawara.
Testing and enhancing the in vitro bioaccessibility and bioavailability of Rosmarinus officinalis extracts with a high level of antioxidant abietanes.
Gastroprotective effect and cytotoxicity of abietane diterpenes from the Chilean Lamiaceae Sphacele chamaedryoides (Balbis) Briq.
Green processes for the extraction of bioactives from Rosemary: Chemical and functional characterization via ultra-performance liquid chromatography-tandem mass spectrometry and in-vitro assays.
Inhibition of anticancer drug efflux transporter P-glycoprotein by rosemary phytochemicals.
Activated glutathione metabolism participates in protective effects of carnosic acid against oxidative stress in neuronal HT22 cells.
Relationship between the antioxidant capacity and effect of rosemary (Rosmarinus officinalis L.) polyphenols on membrane phospholipid order.
Variations in essential oil, phenolic compounds, and antioxidant activity of tunisian cultivated Salvia officinalis L.
Semisynthesis and biological evaluation of abietane-type diterpenes. Revision of the structure of rosmaquinone.
Prophylaxis with carnosol attenuates liver injury induced by intestinal ischemia/reperfusion.
Gastroprotective constituents of Salvia officinalis L.
Carnosic acid and carnosol inhibit adipocyte differentiation in mouse 3T3-L1 cells through induction of phase2 enzymes and activation of glutathione metabolism.
Effect of marinades on the formation of heterocyclic amines in grilled beef steaks.
Liposoluble antioxidants provide an effective radioprotective barrier.
Antioxidant effect rosemary (Rosmarinus officinalis L.) and oregano (Origanum vulgare L.) extracts on TBARS and colour of model raw pork batters.
Carnosol delays chemotherapy-induced DNA fragmentation and morphological changes associated with apoptosis in leukemic cells.
[Studies on the chemical constituents of Salvia miltiorrhiz of Lijiang].
Carnosic acid and carnosol potently inhibit human 5-lipoxygenase and suppress pro-inflammatory responses of stimulated human polymorphonuclear leukocytes.
Polyphenolic transmission to Segureno lamb meat from ewes' diet supplemented with the distillate from rosemary (Rosmarinus officinalis) leaves.
Carnosic acid protects neuronal HT22 Cells through activation of the antioxidant-responsive element in free carboxylic acid- and catechol hydroxyl moieties-dependent manners.
Carnosol, a dietary diterpene, displays growth inhibitory effects in human prostate cancer PC3 cells leading to G2-phase cell cycle arrest and targets the 5'-AMP-activated protein kinase (AMPK) pathway.
Relevance of phenolic diterpene constituents to antioxidant activity of supercritical CO(2) extract from the leaves of rosemary.
Direct determination of carnosic acid in a new active packaging based on natural extract of rosemary.
Supercritical fluid extracts of rosemary leaves exhibit potent anti-inflammation and anti-tumor effects.
Enhanced carnosic acid levels in two rosemary accessions exposed to cold stress conditions.
Sage extract rich in phenolic diterpenes inhibits ultraviolet-induced erythema in vivo.
Characterization of two unknown compounds in methanol extracts of rosemary oil.
Low-density lipoprotein, collagen, and thrombin models reveal that Rosemarinus officinalis L. exhibits potent antiglycative effects.
Screening of plant extracts for antimicrobial activity against bacteria and yeasts with dermatological relevance.
Potentiation of antimicrobial activity of aminoglycosides by carnosol from Salvia officinalis.
Potential of rosemary (Rosemarinus officinalis L.) diterpenes in preventing lipid hydroperoxide-mediated oxidative stress in Caco-2 cells.
Bioactive diterpenes from Orthosiphon labiatus and Salvia africana-lutea.
Abietane diterpenoids from Salvia pachyphylla and S. clevelandii with cytotoxic activity against human cancer cell lines.
Screening of herbal extracts for activation of the human peroxisome proliferator-activated receptor.
Carnosol, a component of rosemary (Rosmarinus officinalis L.) protects nigral dopaminergic neuronal cells.
Rosemary (Rosmarinus officinalis) diterpenes affect lipid polymorphism and fluidity in phospholipid membranes.
Antiplatelet activity of carnosol is mediated by the inhibition of TXA2 receptor and cytosolic calcium mobilization.
Carnosic acid and carnosol, phenolic diterpene compounds of the labiate herbs rosemary and sage, are activators of the human peroxisome proliferator-activated receptor gamma.
Radioprotective-antimutagenic effects of rosemary phenolics against chromosomal damage induced in human lymphocytes by gamma-rays.
Antioxidant and antimicrobial activities of rosemary extracts linked to their polyphenol composition.
Allergic contact dermatitis due to rosemary.
Recovery of antioxidant activity from carnosol quinone: antioxidants obtained from a water-promoted conversion of carnosol quinone.
LC-NMR coupling technology: recent advancements and applications in natural products analysis.
Induction of G2/M phase cell cycle arrest by carnosol and carnosic acid is associated with alteration of cyclin A and cyclin B1 levels.
Development of a triple hyphenated HPLC-radical scavenging detection-DAD-SPE-NMR system for the rapid identification of antioxidants in complex plant extracts.
Carnosol inhibits beta-catenin tyrosine phosphorylation and prevents adenoma formation in the C57BL/6J/Min/+ (Min/+) mouse.
Phenolic and triterpenoid antioxidants from Origanum majorana L. herb and extracts obtained with different solvents.
Carnosol inhibits the invasion of B16/F10 mouse melanoma cells by suppressing metalloproteinase-9 through down-regulating nuclear factor-kappa B and c-Jun.
Antibacterial and resistance modifying activity of Rosmarinus officinalis.
Nitric oxide is synthesized in acute leukemia cells after exposure to phenolic antioxidants and initially protects against mitochondrial membrane depolarization.
Characterization of Cd-induced molecular events prior to cellular damage in primary rat hepatocytes in culture: activation of the stress activated signal protein JNK and transcription factor AP-1.
Carnosic acid, a new class of lipid absorption inhibitor from sage.
Regulation of heme oxygenase-1 expression through the phosphatidylinositol 3-kinase/Akt pathway and the Nrf2 transcription factor in response to the antioxidant phytochemical carnosol.
Screening of the inhibitory effect of vegetable constituents on the aryl hydrocarbon receptor-mediated activity induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin.
Carnosic acid, a component of rosemary (Rosmarinus officinalis L.), promotes synthesis of nerve growth factor in T98G human glioblastoma cells.
Determination of phenolic antioxidant compounds produced by calli and cell suspensions of sage (Salvia officinalis L.).
Antioxidant activity of organic extracts from aqueous infusions of sage.
Phenolic diterpenes, flavones, and rosmarinic acid distribution during the development of leaves, flowers, stems, and roots of Rosmarinus officinalis. Antioxidant activity.
Quantitative determination of phenolic diterpenes in rosemary extracts. Aspects of accurate quantification.
Rapid quantitative enrichment of carnosic acid from rosemary (Rosmarinus officinalis L.) by isoelectric focused adsorptive bubble chromatography.
Subcritical water extraction of antioxidant compounds from rosemary plants.
Protective effect of carnosol on CCl(4)-induced acute liver damage in rats.
Oxidation, reduction, and methylation of carnosic acid by Nocardia.
Inactivation of the human brain muscarinic acetylcholine receptor by oxidative damage catalyzed by a low molecular weight endogenous inhibitor from Alzheimer's brain is prevented by pyrophosphate analogs, bioflavonoids and other antioxidants.
Antioxidant capacity of abietanes from Sphacele salviae.
Semisynthesis of rosmanol and its derivatives. Easy access to abietatriene diterpenes isolated from the genus Salvia with biological activities.
Carnosol, an antioxidant in rosemary, suppresses inducible nitric oxide synthase through down-regulating nuclear factor-kappaB in mouse macrophages.
Evaluation of the effectiveness of Rosmarinus officinalis (Lamiaceae) in the alleviation of carbon tetrachloride-induced acute hepatotoxicity in the rat.
Capillary electrophoretic separation of phenolic diterpenes from rosemary.
Retinoids and carnosol suppress cyclooxygenase-2 transcription by CREB-binding protein/p300-dependent and -independent mechanisms.
Antioxidant activity of chemical components from sage (Salvia officinalis L.) and thyme (Thymus vulgaris L.) measured by the oil stability index method.
Antioxidant properties of phenolic diterpenes from Rosmarinus officinalis.
Apianane terpenoids from Salvia officinalis.
Carnosol-induced apoptosis and downregulation of Bcl-2 in B-lineage leukemia cells.
Dietary ortho phenols that induce glutathione S-transferase and increase the resistance of cells to hydrogen peroxide are potential cancer chemopreventives that act by two mechanisms: the alleviation of oxidative stress and the detoxification of mutagenic xenobiotics.
Response of abietane diterpenes to stress in Rosmarinus officinalis L.: new insights into the function of diterpenes in plants.
Minimum antimicrobial inhibitory concentration of carnosol and of the ethanol extract from Lepichinia hastata (Lamiaceae).
Development of in vitro models for cellular and molecular studies in toxicology and chemoprevention.
Occupational allergic contact dermatitis from carnosol, a naturally-occurring compound present in rosemary.
Mechanisms involved in the chemoprotective effects of rosemary extract studied in human liver and bronchial cells.
Supercritical fluid extraction of natural antioxidants from rosemary:  comparison with liquid solvent sonication.
Inhibition by rosemary and carnosol of 7,12-dimethylbenz[a]anthracene (DMBA)-induced rat mammary tumorigenesis and in vivo DMBA-DNA adduct formation.
An evaluation of the antioxidant and antiviral action of extracts of rosemary and Provençal herbs.
Rosemary extract and carnosol stimulate rat liver glutathione-S-transferase and quinone reductase activities.
Effects of three dietary phytochemicals from tea, rosemary and turmeric on inflammation-induced nitrite production.
Rosemary components inhibit benzo[a]pyrene-induced genotoxicity in human bronchial cells.
Inhibition of lipid peroxidation and superoxide generation by diterpenoids from Rosmarinus officinalis.
Radical intermediates and antioxidants: an ESR study of radicals formed on carnosic acid in the presence of oxidized lipids.
Inhibition of skin tumorigenesis by rosemary and its constituents carnosol and ursolic acid.
Inhibitory effect of carnosic acid on HIV-1 protease in cell-free assays [corrected].
Natural antioxidants as inhibitors of oxygen species induced mutagenicity.
Antioxidative constituents of Rosmarinus officinalis and Salvia officinalis. II. Isolation of carnosic acid and formation of other phenolic diterpenes.
Protection by albumin against the pro-oxidant actions of phenolic dietary components.
Isolation and identification from Salvia officinalis of two diterpenes which inhibit t-butylbicyclophosphoro[35S]thionate binding to chloride channel of rat cerebrocortical membranes in vitro.
Antioxidant and pro-oxidant properties of active rosemary constituents: carnosol and carnosic acid.
Inhibition of mammalian 5-lipoxygenase and cyclo-oxygenase by flavonoids and phenolic dietary additives. Relationship to antioxidant activity and to iron ion-reducing ability.
Traditional medicine of Baja California Sur (Mexico). III. Carnosol: a diterpene antibiotic from Lepechinia hastata.
[Natural and synthetic derivatives of carnosol acid].
Publications by J-Stage
Antiangiogenic Effect of Carnosic Acid and Carnosol, Neuroprotective Compounds in Rosemary Leaves

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEMBL:View
KEGG (GenomeNet):C09069
HMDB (The Human Metabolome Database):HMDB02121
FooDB:FDB014814
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 330.42401123047
Boiling Point 522 to 524°C @ 760 mm Hg
Flash Point TCC Value 186.67 °C TCC
logP (o/w) 2.832 est
Shelf life 6 months (or longer if stored properly.)
Storage notes Refrigerate in tightly sealed containers.
Solubility
water, 9.482 mg/L @ 25 °C (est) Yes

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
None - None found.
S 02 - Keep out of the reach of children.
S 22 - Do not breath dust.
S 24/25 - Avoid contact with skin and eyes.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
natural substances and extractives
Recommendation for carnosol usage levels up to:
not for fragrance use.
Recommendation for carnosol flavor usage levels up to:
not for flavor use.

Safety references

European Food Safety Authority (EFSA) reference(s):

Use of rosemary extracts as a food additive - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food
View page or View pdf

EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :65158
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
Chemidplus:0005957802