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HomeProduct name listStigmasterol

Stigmasterol

Synonym(s):3β-Hydroxy-24-ethyl-5,22-cholestadiene;5,22-Stigmastadien-3β-ol;Stigmasterin;Stigmasterin; Phytosterol; beta-Stigmasterol; D5-Stigmasterol; 110801

  • CAS NO.:83-48-7
  • Empirical Formula: C29H48O
  • Molecular Weight: 412.7
  • MDL number: MFCD00003630
  • EINECS: 201-482-7
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-07 13:31:19
Stigmasterol Structural

What is Stigmasterol?

Description

Stigmasterol is a natural plant sterol that can be isolated from certain seed oils and herbs, including those used for therapeutic purposes. Dietary consumption of phytosterols, including stigmasterol, may have beneficial health effects in adults, particularly against cancer and ulceration. Alternatively, phytosterols may contribute to inflammation and intestinal failure-associated liver disease in young individuals.

Chemical properties

white powder

The Uses of Stigmasterol

Stigmasterol has been used as a phytosterol compound to test its anti-proliferative property in breast cancer cell culture and its effect on liver X receptor-α (LXRA) activation. It may be used as an internal standard for the quantification of yeast cell wall sterols using gas chromatography–mass spectrometry (GC-MS) analysis, and in the preparation of lipid monolayers.

The Uses of Stigmasterol

Plant sterol, used as a precursor in the synthesis of progesterone.

What are the applications of Application

Stigmasterol is a phytosterol with chemical structure similar to cholesterol that exhibits anti-cancer, anti-pyretic, anti-inflammatory and immune-modulating effects

Definition

ChEBI: A 3beta-sterol that consists of 3beta-hydroxystigmastane having double bonds at the 5,6- and 22,23-positions.

General Description

Stigmasterol is a plant sterol that comprises an unsaturated bond between C22 and C23. It is found in foods like margarines and yogurts. Stigmasterol is synthesized from the mevalonate pathway and is present during development stages in plants.

Biochem/physiol Actions

Stigmasterol possesses anti-inflammatory anti-hypercholestrolemic, antitumor and antioxidant functionality. It plays a crucial role in the activation of plasma membrane H+-ATPase and cell proliferation. Variations in stigmasterol and its precursor are noticeable at both the seed and whole plant developmental stages. Stigmasterol may be involved in gravitropism and tolerance to abiotic stress.

storage

+4°C

Purification Methods

Stigmasterol is best purified via the tetrabromide-acetate. The impure sterol (3g) is acetylated with Ac2O (60mL) by refluxing for 1.5hour. The mixture is cooled at 20o for 1hour, and the crude acetate is collected. The acetate (3g) in Et2O (30mL) is then treated with Br2/AcOH (38mL, from 5g Br2 in 100mL AcOH), and after cooling at 6o overnight, the tetrabromoacetate is filtered off and washed with Et2O. After six recrystallisations from CHCl3/MeOH the tetrabromoacetate has m 194-196o. This product (1g) in AcOH (12mL) and Zn dust (1g) is refluxed for 1.5hours, filtered hot, diluted with H2O (30mL) and extracted with Et2O. The extract is washed with dilute aqueous sodium sulfite, then H2O, the extract is dried (Na2SO4) and the stigmasterol acetate (~550mg) is recrystallised (4x) from EtOH and twice from MeOH/CHCl3 (2:1) to give the acetate with m 139-148o. This acetate (400mg) is hydrolysed in boiling 10% alcoholic KOH (1mL) for 1hour. Then H2O (30mL) is added and the mixture is extracted with Et2O. The extract is washed with aqueous Na2CO3, then H2O, the solvent is distilled off and the residue is recrystallised (3x) from 95% EtOH to give ~110mg of pure stigmasterol. It is dried in a vacuum over P2O5 for 3hours at 90o. The purity is checked by NMR. The acetate crystallises from MeOH with m 145o, [] D 25 -56o (c 2, CHCl3). [Byerrum & Ball Biochemical Preparations 7 86 1959, Thornton et al. J Am Chem Soc 62 2006 1940, Colin et al. Anal Chem 51 1661 1979, Beilstein 6 IV 4170.]

Properties of Stigmasterol

Melting point: 165-167 °C (lit.)
Boiling point: 472.07°C (rough estimate)
alpha  -50 º (c=2, CHCl3)
Density  0.9639 (rough estimate)
refractive index  1.5000 (estimate)
storage temp.  -20°C
solubility  chloroform: soluble50 mg/ml
form  Powder
pka 15.03±0.70(Predicted)
color  White
Water Solubility  insoluble
λmax 226nm(MeOH)(lit.)
Merck  14,8815
BRN  2568182
CAS DataBase Reference 83-48-7(CAS DataBase Reference)
NIST Chemistry Reference Stigmasterol(83-48-7)
EPA Substance Registry System Stigmasterol (83-48-7)

Safety information for Stigmasterol

Signal word Danger
Pictogram(s)
ghs
Skull and Crossbones
Acute Toxicity
GHS06
ghs
Health Hazard
GHS08
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H331:Acute toxicity,inhalation
H336:Specific target organ toxicity,single exposure; Narcotic effects
H351:Carcinogenicity
H372:Specific target organ toxicity, repeated exposure
H412:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes P201:Obtain special instructions before use.
P273:Avoid release to the environment.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P308+P313:IF exposed or concerned: Get medical advice/attention.

Computed Descriptors for Stigmasterol

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