Gamma oryzanol Chemical Properties

Melting point:

135-137°C

Boiling point:

571.92°C (rough estimate)

Density 

0.9751 (rough estimate)

refractive index 

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 

14,6886

LogP

13.205 (est)

CAS DataBase Reference

11042-64-1(CAS DataBase Reference)

Safety Information

RIDADR 

UN 2811 6.1/PG II

RTECS 

RN0050000

HS Code 

3822.19.0080

HazardClass 

6.1

PackingGroup 

II

Toxicity

LD50 oral in rat: > 25gm/kg

MSDS

• Language:English Provider:gamma-Oryzanol

Gamma oryzanol Usage And Synthesis

Description

Gamma 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.

Chemical Properties

White to Off-White Solid

Occurrence

Gamma 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.

Uses

Gamma 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.

Preparation

Extraction 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%

Definition

ChEBI: Gamma-Oryzanol (TN) is a triterpenoid.

General Description

Gamma 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.

Side effects

Gamma oryzanol has no side effects for horses, dogs or humans.
Toxicity studies on animals demonstrate that gamma oryzanol is a very safe compound. No significant side-effects have been reported in human trials at the above noted recommended dosage.
Some research suggests that gamma oryzanol taken in moderately high amounts (up to 600 mg per day) for several months can cause dry mouth, sleepiness, hot flushes, irritability, and light headedness in some individuals.

Safety Profile

A poison by skin contact. Moderately toxic by intravenous route. Low toxicity by ingestion. Experimental reproductive effects. When heated to decompositionit emits acrid smoke and irritating vapors.

Dosage

A typical dosage of gamma oryzanol is 500 mg daily.

Gamma oryzanol(11042-64-1)Related Product Information

• Nicotinic acid
• COD LIVER OIL
• ORYZANOL
• 4-Aminobutyric acid
• Isobutyl cinnamate
• Ethyl 4-hydroxy-3-methoxycinnamate
• 4-tert-Butylcyclohexyl acetate
• CYCLOHEXYL CINNAMATE
• Pentyl cinnamate
• CYCLOARTENYL FERULATE
• Isopropyl ferulate
• HEPTYL CINNAMATE
• N-NONYL ACRYLATE
• OCTYL CINNAMATE
• 4-TERT-BUTYLCYCLOHEXYL ACRYLATE
• Gamma oryzanol
• SPIRO[2.5]OCTANE