Stigmasterol Chemical Properties

Melting point:

165-167 °C (lit.)

alpha 

-50 º (c=2, CHCl3)

Boiling point:

472.07°C (rough estimate)

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

LogP

10.072 (est)

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

Hazard Codes 

Xn,Xi

Risk Statements 

22-38-40-48/20/22-36/37/38-67-36/38-20-63

Safety Statements 

22-24/25-36/37-36-26

RIDADR 

UN 1888 6.1/PG 3

WGK Germany 

3

RTECS 

WJ2447500

HS Code 

29309070

Hazardous Substances Data

83-48-7(Hazardous Substances Data)

MSDS

• Language:English Provider:Stigmasta-5,22-dien-3beta-ol
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Stigmasterol Usage And Synthesis

Description

Stigmasterol is a kind of plant sterol or phytosterol. It is a kind of steroid derivative containing the hydroxyl group, unsaturated bonds, and alkyl group. It mainly exists in the fats and oils of soybean, Calabar bean, and rape seed as well as some kinds of vegetables, legumes and nuts. It can be used for the manufacture of semisynthetic progesterone which is a valuable human hormone. It can also be used in the biosynthesis of androgen, estrogen, and corticoids. Moreover, it can be used for the manufacture of vitamin D3 and cortisone. As a dietary supplement, it can reduce the cholesterol contained in the human body, thus boosting the health state of our body. 

References

https://en.wikipedia.org/wiki/Stigmasterol
https://pubchem.ncbi.nlm.nih.gov/compound/Stigmasterin#section=Top

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

Uses

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

Uses

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.

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.]

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