Stigmasterol

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title: "Stigmasterol" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["phytosterols"] topic_path: "general/phytosterols" source: "https://en.wikipedia.org/wiki/Stigmasterol" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 450634143 | ImageFile=Stigmasterin.svg | ImageClass = skin-invert-image | ImageSize=220px | ImageFile1 = Stigmasterin molecule ball.png | ImageClass1 = bg-transparent | ImageSize1 = 250 | ImageAlt1 = Ball-and-stick model of stigmasterol | IUPACName = Stigmasta-5,22-dien-3β-ol | SystematicName = (1R,3aS,3bS,7S,9aR,9bS,11aR)-1-[(2R,3E,5S)-5-Ethyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-7-ol | OtherNames= Stigmasterin; Wulzen anti-stiffness factor |Section1={{Chembox Identifiers | CASNo_Ref = | CASNo=83-48-7 | PubChem=5280794 | ChEMBL_Ref = | ChEMBL = 400247 | UNII_Ref = | UNII = 99WUK5D0Y8 | ChEBI_Ref = | ChEBI = 28824 | SMILES=CCC(C=CC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)C(C)C | ChemSpiderID_Ref = | ChemSpiderID = 4444352 | InChI = 1/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h8-10,19-21,23-27,30H,7,11-18H2,1-6H3/b9-8+/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1 | InChIKey = HCXVJBMSMIARIN-PHZDYDNGBL | StdInChI_Ref = | StdInChI = 1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h8-10,19-21,23-27,30H,7,11-18H2,1-6H3/b9-8+/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1 | StdInChIKey_Ref = | StdInChIKey = HCXVJBMSMIARIN-PHZDYDNGSA-N |Section2={{Chembox Properties | C=29 | H=48 | O=1 | Appearance= White solid | Density= | BoilingPt= | MeltingPtC=160 to 164 | MeltingPt_ref = | Solubility=Insoluble |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt =

Stigmasterol – a plant sterol (phytosterol) – is among the most abundant of plant sterols, having a major function to maintain the structure and physiology of cell membranes. In the European Union, it is a food additive listed with E number E499, and may be used in food manufacturing to increase the phytosterol content, potentially lowering the levels of LDL cholesterol.

Discovery

Once called Wulzen factor in the mid-20th century, stigmasterol was discovered by the University of California physiologist Rosalind Wulzen (born 1886).

Natural occurrences

Stigmasterol is an unsaturated phytosterol occurring in the plant fats or oils of numerous plants,

Stigmasterol is a constituent of various vegetables, legumes, nuts, seeds, and unpasteurized milk. Pasteurization will inactivate stigmasterol. Edible oils contains higher amount than vegetables.

Uses

Stigmasterol is a food additive in manufactured food products in the United Kingdom and European Union.

It was introduced as a precursor by Percy Lavon Julian for industrial large-scale manufacture of semisynthetic progesterone, a valuable human hormone that plays an important physiological role in the regulatory and tissue rebuilding mechanisms related to estrogen effects, as well as acting as an intermediate in the biosynthesis of androgens, estrogens, and corticoids. It is also used as the precursor of vitamin D3.

The Upjohn company used stigmasterol as the starting raw material for commercial synthesis of cortisone in 1959.

Research

As one of the major phytosterols, stigmasterol is included among sterol compounds in the diet having potential to reduce the risk of cardiovascular diseases.

Potential precursor of boldenone

Being a steroid, stigmasterol is precursor of anabolic steroid boldenone. Boldenone undecylenate is commonly used in veterinary medicine to induce growth in cattle, but it is also one of the most commonly abused anabolic steroids in sports. This led to suspicion that some athletes testing positive for boldenone didn't consume the steroid itself, but rather consumed foods rich in stigmasterol. This turned out not to be the case, as humans do not appear to convert stigmasterol from food into boldenone. Calves have been reported to convert photosterol into boldenone, but even then the amounts in urine are below doping limits.

References

References

  1. [http://chemicalland21.com/lifescience/phar/STIGMASTEROL.htm Stigmasterol], ChemicalLand21.com
  2. (July 2017). "Emerging roles for conjugated sterols in plants". Progress in Lipid Research.
  3. (November 2017). "Phytosterols in the Treatment of Hypercholesterolemia and Prevention of Cardiovascular Diseases". Arquivos Brasileiros de Cardiologia.
  4. "Rosalind Wulzen (b. 1886)". Smithsonian Institution.
  5. (1990). "Constituents of Mirabilis jalapa". Fitoterapia.
  6. (December 2008). "Contents of phytosterols in vegetables and fruits commonly consumed in China". Biomedical and Environmental Sciences.
  7. (1 March 2018). "EU-approved additives and E Numbers".
  8. (October 1977). "A convenient synthesis of progesterone from stigmasterol". The Journal of Organic Chemistry.
  9. (6 February 2007). "Nova Transcripts: Forgotten Genius". PBS.org.
  10. "Giants of the Past". lipidlibrary.aocs.org.
  11. (1987). "Synthesis of vitamin D3 and related compounds". Medicinal Research Reviews.
  12. (December 1992). "Steroids, the steroid community, and Upjohn in perspective: a profile of innovation". Steroids.
  13. Soy Infocenter. (2009). "History of Soybean and Soyfoods in Mexico and Central America (1877-2009)". Soyinfo Center.
  14. (July 2007). "Phytosterol consumption and the anabolic steroid boldenone in humans: a hypothesis piloted". Food Additives and Contaminants.
  15. (October 2007). "Boldenone, boldione, and milk replacers in the diet of veal calves: the effects of phytosterol content on the urinary excretion of boldenone metabolites". Journal of Agricultural and Food Chemistry.
  16. (March 2007). "Excretion profile of boldenone in urine of veal calves fed two different milk replacers". Analytica Chimica Acta.

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phytosterols