Campesterol

Campesterol
Compound Structure:
Synonyms: CAMPESTEROL;Campesterin;Campest-5-en-3beta-ol;24(R)-methylcholesterol;Campasterol;Ergost-5-en-3-ol, (3beta,24R)-;24alpha-Methylcholesterol;Ergost-5-en-3beta-ol, (24R)-;(24R)-5-Ergosten-3b-ol;(24R)ergost-5-en-3beta-ol
Compound ID: NMPC-715
PubChem ID:

173183

Molecular Formula: C28H48O
Canonical SMILES: CC(C)C(C)CCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C
InChIKey: SGNBVLSWZMBQTH-PODYLUTMSA-N
About the compound:

Campesterol is a type of phytosterol, a category of plant-derived sterols with a structure similar to cholesterol found in animals. Chemically, it is classified as a 3beta-sterol, a 3beta-hydroxy-Delta(5)-steroid, and a C28-steroid. In biological terms, it serves as a metabolite in mice and can be derived from a hydride of campestane. As a natural product, campesterol is found in various organisms, including Haplophyllum bucharicum and Bugula neritina. Structurally, it is a sterol derivative characterized by a hydroxyl group at the C-3 position and a double bond between the 5th and 6th carbon atoms in the B ring of the steroid skeleton. The rest of its structure is saturated, making it the simplest form of sterol. Campesterol is present in many everyday foods, though typically in low concentrations. Common sources include bananas, pomegranates, peppers, coffee, grapefruits, cucumbers, onions, oats, potatoes, and lemongrass, with concentrations ranging from approximately 1–7 mg per 100 g of the edible portion. Notably, canola and corn oils contain higher levels, ranging from 16–100 mg per 100 g. The levels of campesterol in plants can vary based on geographic location, environmental conditions, and specific plant strains. Efforts are underway to genetically engineer plant strains to produce higher levels of campesterol and other beneficial phytosterols. Campesterol was first isolated from rapeseed (Brassica campestris), which is reflected in its name. Since the 1950s, plant sterols like campesterol have been recognized for their ability to lower low-density lipoprotein (LDL) levels and overall cholesterol. They exert this effect by competing with cholesterol, thereby reducing its absorption in the human intestine. Additionally, phytosterols may influence intestinal cells directly, affecting transporter proteins, and may also impact cholesterol metabolism in the liver. Serum levels of campesterol, as well as the ratio of campesterol to cholesterol, have been studied as potential indicators of cardiac risk. While some studies suggest that higher levels of campesterol may correlate with lower cardiac risk, extremely high levels, such as those seen in genetic disorders like sitosterolemia, are associated with higher risk. However, research findings on this topic have been mixed. A 2012 meta-analysis indicated no clear relationship between blood levels of campesterol (or sitosterol) and cardiovascular disease risk, suggesting that other dietary and lifestyle factors might confound these results. For instance, a diet rich in fruits and nuts, which increases campesterol levels, may be part of a healthier Mediterranean-style diet, contributing to lower cardiac risk due to a variety of factors.

GHS Hazard Statements

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]

H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

400.7 g/mol

XLogP3-AA

8.8

Hydrogen Bond Donor Count

1

Hydrogen Bond Acceptor Count

1

Rotatable Bond Count

5

Exact Mass

400.370516150 g/mol

Monoisotopic Mass

400.370516150 g/mol

Topological Polar Surface Area

20.2Ų

Heavy Atom Count

29

Formal Charge

0

Complexity

620

Isotope Atom Count

0

Defined Atom Stereocenter Count

9

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Solid; [Merck Index] White crystalline solid; [Sigma-Aldrich MSDS]

Melting Point

157.5 °C

Source: PubChem            

Source Species: Smilax kraussiana
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