Gamma-Oryzanol

HCID 5282164

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

gamma-Oryzanolgamma Oryzanol11042-64-1GammarizaOliverSST9XCL51MDTXSID6021084RefChem:856958600-960-6Cycloartenyl ferulategamma-OrizanolHI-Z
Show more names
Γ-ORYZANOLozγ-OryzanolGu Weisu.gamma.-Orizanol
21238-33-5Gamma oryzanol [JAN]UNII-SST9XCL51MCycloartenol Trans-FerulateCycloartenol ferulateOryzanol A3-O-Ferulylcycloartenol3PQR2YON9T

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

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

Safety & regulation

GHS classification

GHS Classification · 6 items

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 · 2 items

Chemical: .gamma.-Oryzanol

Gamma-oryzanol: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and Categories · 2 items

Acute Tox. 2 (100%)

Not Classified

Regulatory information

Regulatory Information · 2 items

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

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

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

Use ClassificationCosmetics -> Skin conditioning; Antistatic
Applications · 4 items

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 · 1 item

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

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
湖北金梭生物科技有限公司00123456789 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]

Additional notes

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

Related reactions

2 records

Compound notes

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