Basic information
- CAS
11042-64-1- Standard SMILES
COc1cc(/C=C/C(=O)O[C@H]2CC[C@]34C[C@]35CC[C@]3(C)[C@@H]([C@H](C)CCC=C(C)C)CC[C@@]3(C)[C@@H]5CC[C@H]4C2(C)C)ccc1O- InChIKey
FODTZLFLDFKIQH-FSVGXZBPSA-N- Molecular formula
- C40H58O4
- Average molar mass
- 602.9 g/mol
- Monoisotopic mass
- 602.43351033
Names & identifiers
- Preferred name
- Gamma-Oryzanol
- IUPAC
- [(1S,3R,6S,8R,11S,12S,15R,16R)-7,7,12,16-tetramethyl-15-[(2R)-6-methylhept-5-en-2-yl]-6-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
- English name
- Gamma oryzanol
- Molecular formula
- C40H58O4
- Molecular weight
- 602.89
Names & synonyms
Show more names
Database identifiers
- CAS
11042-64-1、21238-33-5- PubChem CID
- 5282164
- ChEMBL
CHEMBL388595- ChEBI
CHEBI:32345- UNII
- 3PQR2YON9T
- EC Number
- 244-285-1、600-960-6
- Nikkaji
- J1.737.041C、J442.513H
Properties
Computed structural properties
- XLogP
- 12.1
- Topological polar surface area
- 55.8 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 9
- Heavy atoms
- 44
- Formal charge
- 0
- Complexity
- 1,150
Physicochemical properties
- Melting point
- 135 · 135-137°C
- Boiling point
- 571.92 °C · 571.92°C (rough estimate)
- Density
- 0.9751 · 0.9751 (rough estimate)
- refractive index
- 1.476 · 1.4760 (estimate)
- storage temp.
- Sealed in dry,Room Temperature
- Water Solubility
- Practically insoluble in water
- solubility
- Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
- form
- powder to crystaline
- color
- White to Light yellow
- Odor
- little or no odor
- Merck
- 14 · 14,6886
- Major Application
- pharmaceutical (small molecule)
- Cosmetics Ingredients Functions
- ANTISTATICSKIN CONDITIONING
- InChIKey
- FODTZLFLDFKIQH-PGYKLSNGNA-N
- SMILES
- C123CC[C@]4(C)[C@H](CC[C@@]4(C)C1CCC1C(C)(C)[C@@H](OC(=O)/C=C/C4=CC=C(O)C(OC)=C4)CC[C@]21C3)C(C)CC/C=C(\C)/C |&1:3,5,8,17,34,r|
- LogP
- 13.205 · 13.205 (est)
- CAS DataBase Reference
- 11042 · 11042-64-1(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 9 XCL51M · SST9XCL51M
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 310 · H310
- Precautionary statements
- 501 · P501-P270-P262-P264-P280-P361+P364-P302+P352+P310-P405
- RIDADR
- 2811 · UN 2811 6.1/PG II
- WGK Germany
- 3 · WGK 3
- RTECS
- 50000 · RN0050000
- HS Code
- 3822.19 · 3822.19.0080
- HazardClass
- 6.1 · 6.1
- PackingGroup
- II
- Storage Class
- 6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- Hazard Classifications
- 2 Dermal · Acute Tox. 2 Dermal
- Toxicity
- 50 oral · LD50 oral in rat: > 25gm/kg
Safety & regulation
GHS classification
GHS Classification
Danger
H310 (100%): Fatal in contact with skin [Danger Acute toxicity, dermal]
P262, P264, P270, P280, P302+P352, P316, P321, P361+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 57 reports by companies from 1 notifications to the ECHA C&L Inventory.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Not Classified;Reported as not meeting GHS hazard criteria by 1 of 1 companies. For more detailed information, please visit ECHA C&L website.
Hazard information
Regulatory Information
Chemical: .gamma.-Oryzanol
Gamma-oryzanol: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and Categories
Acute Tox. 2 (100%)
Not Classified
Regulatory information
Regulatory Information
Chemical: .gamma.-Oryzanol
Gamma-oryzanol: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- wgk
- WGK 3
- rtecs
- RN0050000
- ridadr
- UN 2811 6.1/PG II
- hs_code
- 3822.19.0080
- Toxicity
- LD50 oral in rat: > 25gm/kg
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_class
- 6.1
- Storage Class
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- packing_group
- II
- Hazard statements
- H310
- Hazard Classifications
- Acute Tox. 2 Dermal
- Precautionary statements
- P501-P270-P262-P264-P280-P361+P364-P302+P352+P310-P405
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief.
Substances that lower the levels of certain LIPIDS in the BLOOD. They are used to treat HYPERLIPIDEMIAS.
Uses & manufacturing
Applications
DescriptionGamma oryzanol is a lipid fraction derived from rice-bran oil. Oryzanol was first isolated from rice-bran oil in the 1950s. Several lipid fractions were isolated from the oil.The third (gamma) fraction isolated was oryzanol.It is made up of a mixture of ferulic acid esters and plant sterols. Similar in structure to cholesterol, the phytosterols and triterpenes that comprise oryzanol include campesterol, stigmasterol, beta sitosterol, cycloartanol, and cycloartenol. Because phytosterols are poorly absorbed, it has been suggested that they may reduce blood cholesterol by inhibiting intestinal cholesterol absorption.In contrast, the ferulic acid portion of gamma oryzanol is easily absorbed into the body's tissues. Ferulic acid also has demonstrated antioxidant properties in vitro.
OccurrenceGamma oryzanol is found in rice-bran oil, which is commercially available in Japan for use in salad oils and frying.Crude rice-bran oil contains approximately 1.56% oryzanol.Of the 180 mg of plant sterols found in the typical American diet,about 4% is gamma-oryzanol.One cup of brown rice provides 18 mg gamma oryzanol, whereas white rice provides 4mg. The ferulic acid portion of gamma oryzanol is naturally found in the bran of cereals, and in fruits and vegetables.Ferulic acid is also a metabolite of caffeic acid found in coffee.
UsesGamma Oryzanol is a mixture of 6 substances derived from rice bran oil, including sterols and ferulic acid, called Cycloartanyl Ferulate or Triterpene alcohol ferulate. It has been approved in Japan for several conditions, including menopausal symptoms, mild anxiety, stomach upset, and high cholesterol. In the US, it is widely used as a sports supplement, as well as for reducing cholesterol. gamma oryzanol is widely used as a food additive, pharmaceutical material. In cosmetic area, the application to creams and sunscreens exploiting its skin age resistor function and ultraviolet absorbing effect.
General DescriptionGamma oryzanol is found in the by-products of the rice industry, such as rice bran and rice bran oil. It exhibits a wide range of biological activities, including anticarcinogenic, anti-inflammatory, antihyperlipidemic, and neuroprotective properties, which are primarily due to its high antioxidant capacity.
Preparation methods
PreparationExtraction of gamma oryzanol from processes oil. Gamma oryzanol can be extracted by liquid-liquid extraction method by using organic solvent or by using supercritical extraction method. The following procedure was followed to extract gamma oryzanol from the oil.Rice Bran Oil (1 kg)→NaOH and water was added→Stirred and stored for one day at room temperature→Acidified to pH 4 using H2SO4→Heated to 80°C→50g NaCl was added→Oily layer was obtained→ Methanol was added→ Mixture was cooled to 0°C for 2 hrs.→ Waxy component precipitated→ Solution of 5g H2SO4 in 300 ml methanol→ Stored for one day→ Stirred at 40°C to remove/evaporate methanol→ To 100g residue 100g n-hexane was added→ Solvent Distillation→ Treatment of 100 ml methanol was given→ Residue was extracted 3 times with 50ml 0.5N→ methanolicNaOH→ Neutralised with methanolic acetic acid to pH 6.8-7→ Stored to precipitate gamma oryzanol.The yield of gamma oryzanol was found to be 2.2%
Suppliers100 total
Additional notes
DefinitionChEBI: Gamma-Oryzanol (TN) is a triterpenoid.
Related reactions
Compound notes
Loading…