| Identification | More | [Name]
Stigmasterol | [CAS]
83-48-7 | [Synonyms]
(24S)-5,22-STIGMASTADIEN-3BETA-OL
3BETA-HYDROXY-24-ETHYL-5,22-CHOLESTADIENE
[3B-HYDROXY-24-ETHYL-D] ZZ-CHOLESTADIENE
5,22-CHOLESTADIEN-24BETA-ETHYL-3BETA-OL
5,22-CHOLESTADIEN-24B-ETHYL-3BETA-OL
5,22-STIGMASTADIEN-3-BETA-OL
PHYTOSTEROL
STIGMASTA-5,22-DIEN-3BETA-OL
STIGMASTA-5,22-DIEN-3-OL, (3BETA)-
STIGMASTERIN
STIGMASTEROL
(22E)-Stigmasta-5,22-dien-3-ol
5,22-Cholestadien-24-ethyl-3beta-ol
beta-Stigmasterol
DELTA5,22-Stigmastadien-3beta-ol
I-Stigmasterol
Stigmasta-5,22-dien-3-ol
Stigmasta-5,22-dien-3-ol, (3beta,22E)-
3β-Hydroxy-24-ethyl-5,22-cholestadiene
5,22-Stigmastadien-3β-ol | [EINECS(EC#)]
201-482-7 | [Molecular Formula]
C29H48O | [MDL Number]
MFCD00003630 | [Molecular Weight]
412.69 | [MOL File]
83-48-7.mol |
| Chemical Properties | Back Directory | [Appearance]
white powder | [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. ]
0-6°C | [solubility ]
chloroform: soluble50 mg/ml | [form ]
Powder | [pka]
15.03±0.70(Predicted) | [color ]
White | [Water Solubility ]
insoluble | [λmax]
226nm(MeOH)(lit.) | [Merck ]
8814 | [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]
83-48-7(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R38:Irritating to the skin.
R40:Limited evidence of a carcinogenic effect.
R48/20/22:Harmful: danger of serious damage to health by prolonged exposure through inhalation and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36/37:Wear suitable protective clothing and gloves .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RIDADR ]
UN 1888 6.1/PG 3 | [WGK Germany ]
3
| [RTECS ]
WJ2447500 | [HS Code ]
29309070 | [Hazardous Substances Data]
83-48-7(Hazardous Substances Data) |
| Questions And Answer | Back Directory | [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
|
| Hazard Information | Back Directory | [Chemical Properties]
white powder | [Uses]
Plant sterol, used as a precursor in the synthesis of progesterone. | [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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