CAS Number11042-64-1
SynonymsCycloartenylferulate; (3b,9b)-9,19-cyclolanost-24-en-3-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate; (3β,9β)-9,19-cyclolanost-24-en-3-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate; gamma-Oryzanol; (3β,9β)-9,19-Cyclolanost-24-en-3-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)acrylate; MFCD00867548; Oryzanol A; γ-Oryzanol; EINECS 244-285-1
Molecular FormulaC40H58O4
Molecular Weight602.89
Purity98%
Density1.1±0.1 g/cm3
Boiling Point663.2±40.0 °C at 760 mmHg
Melting Point135-137°C
AppearanceWhite crystalline powder
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 11042-64-1 |
| Catalog No. | 2A-9010683 |
| Chinese Name | 谷维素 |
| Synonyms | Cycloartenylferulate; (3b,9b)-9,19-cyclolanost-24-en-3-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate; (3β,9β)-9,19-cyclolanost-24-en-3-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate; gamma-Oryzanol; (3β,9β)-9,19-Cyclolanost-24-en-3-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)acrylate; MFCD00867548; Oryzanol A; γ-Oryzanol; EINECS 244-285-1 |
| Molecular Formula | C40H58O4 |
| Molecular Weight | 602.89 |
| Purity | 98 |
| Density | 1.1±0.1 g/cm3 |
| Boiling Point | 663.2±40.0 °C at 760 mmHg |
| Melting Point | 135-137°C |
| Appearance | White crystalline powder |
| Water Solubility | Water solubility: virtually insoluble; soluble in: |
| Storage Condition | Light-sealed packaging in non-toxic plastic bags o |
| Packaging | II |
| Application | γ-Oryzanol potently inhibits DNA methyltransferases (DNMTs) in the mouse striatum. Inhibits DNMT1 and DNMT3a with IC50 of 3.2 μM and 22.3 μM, respectively. |
| HTC | 2932999099 |
| SMILES | COc1cc(C=CC(=O)OC2CCC34CC35CCC3(C)C(C(C)CCC=C(C)C)CCC3(C)C5CCC4C2(C)C)ccc1O |
| InChI | InChI=1S/C40H58O4/c1-26(2)10-9-11-27(3)29-18-20-38(7)33-16-15-32-36(4,5)34(19-21-39(32)25-40(33,39)23-22-37(29,38)6)44-35(42)17-13-28-12-14-30(41)31(24-28)43-8/h10,12-14,17,24,27,29,32-34,41H,9,11,15-16,18-23,25H2,1-8H3/b17-13+/t27-,29-,32+,33+,34+,37-,38+,39-,40+/m1/s1 |
| InChI Key | FODTZLFLDFKIQH-OINQMCCZSA-N |
| NACRES Code | NA.24 |
| UNSPSC | 41116107 |
| MSDS | msds/10683_1_11042_64_1.pdf |
| Bioactivity | γ-Oryzanol is a potent DNA methyltransferases (DNMTs) inhibitor in the striatum of mice. γ-Oryzanol significantly inhibits the activities of DNMT1 (IC50=3.2 μM), DNMT3a (IC50=22.3 μM). Related Catalog Signaling Pathways >> Epigenetics >> DNA Methyltransferase Research Areas >> Metabolic Disease Target DNMT1:3.2 μM (IC50) DNMT3A:22.3 μM (IC50) In Vitro γ-Oryzanol significantly inhibits the activities of DNMT1 (IC50=3.2 μM), DNMT 3a (IC50=22.3 μM) and DNMT 3b (maximum inhibition 57%). In contrast, the inhibitory activity of Ferulic acid, a metabolite of γ-Oryzanol, is much lower than that of γ-Oryzanol. Furthermore, γ-Oryzanol acts as a partial antagonist against ERRγ, which primarily serves as a positive regulator for DNMT1 production, and consequently decreased the activity of DNMT1[1]. In Vivo The brown rice-specific bioactive component γ-Oryzanol, a mixture of ferulic acid ester and several phytosterols, attenuates the preference for dietary fat via a decrease in hypothalamic endoplasmic reticulum (ER) stress. γ-Oryzanol ameliorates HFD-induced DNA hypermethylation of the promoter region of D2R in the striatum of mice. γ-Oryzanol might regulate levels of DNMTs in a striatum-specific manner. γ-Oryzanol partially decreases ERRγ activity (an approximately 40% reduction of the innate value). Oral administration of γ-Oryzanol to male mice by gavage significantly attenuates the preference for an HFD (93% of the values for vehicle-treated mice), resulting in an apparent attenuation of body weight gain[1]. Kinase Assay To assess the inhibitory activity of each compound on DNA methylation, the formation of S-adenosyl-l-homocysteine (SAH) is measured in the presence of each compound (20 μM for screening assays),S-adenosyl methionine (SAM; 10 μM) and DNMT substrate (4 ng/μL) at 37°C for 90 min. To evaluate the Michaelis-Menten kinetics, DNMT1 (20 μM) is incubated with γ-Oryzanol, SAM (5 μM) and the indicated concentration of poly dI-dC at 37°C for 90 min. DNMT3a (100 μM) and DNMT3b (100 μM) are incubated with γ-Oryzanol, SAM (5 μM) and the indicated concentration of poly dG•dC at 37°C for 120 min. The assays are performed in quadruplicate. Extracted protein (0.75 mg/mL) is incubated with SAM (5 μM), poly dI-dC (5 μg/mL), and poly dG•dC (5 μg/mL) at 40°C for 120 min, and SAH formation is measured[1]. Animal Admin Mice[1] Seven-week-old male C57BL/6J mice are used. To evaluate the preference for the HFD, γ-Oryzanol is administrated to 8-week-old mice by gavage during the food choice test. For the other experiments, an HFD containing 0.4% γ-Oryzanol is manufactured as pellets. After 12 weeks of feeding, tissue is collected from the striatum and hypothalamus. The daily intake of γ-Oryzanol, estimated from the mean food intake of the mice, is approximately 320 μg/g body weight. The doses of γ-Oryzanol are determined. References [1]. Kozuka C, et al. Impact of brown rice-specific γ-oryzanol on epigenetic modulation of dopamine D2 receptors in brain striatum in high-fat-diet-induced obesity in mice. Diabetologia. 2017 Aug;60(8):1502-1511. Chemical & Physical Properties Density 1.1±0.1 g/cm3 Boiling Point 663.2±40.0 °C at 760 mmHg Melting Point 135-137°C Molecular Formula C40H58O4 Molecular Weight 602.886 Flash Point 193.8±20.8 °C Exact Mass 602.433533 PSA 55.76000 LogP 12.85 Vapour Pressure 0.0±2.1 mmHg at 25°C Index of Refraction 1.570 InChIKey FODTZLFLDFKIQH-OINQMCCZSA-N SMILES COc1cc(C=CC(=O)OC2CCC34CC35CCC3(C)C(C(C)CCC=C(C)C)CCC3(C)C5CCC4C2(C)C)ccc1O |
| Use of | γ-Oryzanol is a potent DNA methyltransferases (DNMTs) inhibitor in the striatum of mice. γ-Oryzanol significantly inhibits the activities of DNMT1 (IC50=3.2 μM), DNMT3a (IC50=22.3 μM). Properties Name Gamma-Oryzanol Synonym More Synonyms γ-Oryzanol Biological Activity Description γ-Oryzanol is a potent DNA methyltransferases (DNMTs) inhibitor in the striatum of mice. γ-Oryzanol significantly inhibits the activities of DNMT1 (IC50=3.2 μM), DNMT3a (IC50=22.3 μM). Related Catalog Signaling Pathways >> Epigenetics >> DNA Methyltransferase Research Areas >> Metabolic Disease DNMT1:3.2 μM (IC50) DNMT3A:22.3 μM (IC50) In Vitro γ-Oryzanol significantly inhibits the activities of DNMT1 (IC50=3.2 μM), DNMT 3a (IC50=22.3 μM) and DNMT 3b (maximum inhibition 57%). In contrast, the inhibitory activity of Ferulic acid, a metabolite of γ-Oryzanol, is much lower than that of γ-Oryzanol. Furthermore, γ-Oryzanol acts as a partial antagonist against ERRγ, which primarily serves as a positive regulator for DNMT1 production, and consequently decreased the activity of DNMT1[1]. In Vivo The brown rice-specific bioactive component γ-Oryzanol, a mixture of ferulic acid ester and several phytosterols, attenuates the preference for dietary fat via a decrease in hypothalamic endoplasmic reticulum (ER) stress. γ-Oryzanol ameliorates HFD-induced DNA hypermethylation of the promoter region of D2R in the striatum of mice. γ-Oryzanol might regulate levels of DNMTs in a striatum-specific manner. γ-Oryzanol partially decreases ERRγ activity (an approximately 40% reduction of the innate value). Oral administration of γ-Oryzanol to male mice by gavage significantly attenuates the preference for an HFD (93% of the values for vehicle-treated mice), resulting in an apparent attenuation of body weight gain[1]. Animal Admin Mice[1] Seven-week-old male C57BL/6J mice are used. To evaluate the preference for the HFD, γ-Oryzanol is administrated to 8-week-old mice by gavage during the food choice test. For the other experiments, an HFD containing 0.4% γ-Oryzanol is manufactured as pellets. After 12 weeks of feeding, tissue is collected from the striatum and hypothalamus. The daily intake of γ-Oryzanol, estimated from the mean food intake of the mice, is approximately 320 μg/g body weight. The doses of γ-Oryzanol are determined. References [1]. Kozuka C, et al. Impact of brown rice-specific γ-oryzanol on epigenetic modulation of dopamine D2 receptors in brain striatum in high-fat-diet-induced obesity in mice. Diabetologia. 2017 Aug;60(8):1502-1511. Chemical & Physical Properties Molecular Formula C40H58O4 Exact Mass 602.433533 PSA 55.76000 LogP 12.85 Index of Refraction 1.570 InChIKey FODTZLFLDFKIQH-OINQMCCZSA-N |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 20.0% |
| Transport Info | Product name: Purity: 98.0% |
| MSDS Transport Info | Module 14. Shipping information United Nations classification: Item 1 Poisons. UN number: 2811 Proper Shipping Name: Toxic Solid, Organic, Not Otherwise Specified Packing grade: II |
| Related Products in Polymer Intermediates | ||
|---|---|---|
| Vinyl acetate | 108-05-4 | 2A-9008902 |
| Alodane | 2550-75-6 | 2A-9009119 |
| Anisodamine | 55869-99-3 | 2A-0201327 |
| Benziodarone | 68-90-6 | 2A-9009354 |
| Codactide | 22572-04-9 | 2A-9009895 |
| Gynostemma Pentaphyllum P.E. | 2A-301894 | 2A-9010811 |
| Imazodan | 84243-58-3 | 2A-9010917 |
| Imitrodast | 114686-12-3 | 2A-9010931 |
| Iodamide | 440-58-4 | 2A-9010966 |
| Lodazecar | 87646-83-1 | 2A-9011209 |
| Browse all Polymer Intermediates products » | ||
Phone:
630-322-8886
630-322-8887
Email:
Office Locations:
Chicago, IL, USA
San Francisco, CA, USA
EN
SDS