Ergosterol

(1R,3aR,7S,9aR,9bS,11aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1H,2H,3H,3aH,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ol

C28H44O (396.3392)


Ergosterol is a phytosterol consisting of ergostane having double bonds at the 5,6-, 7,8- and 22,23-positions as well as a 3beta-hydroxy group. It has a role as a fungal metabolite and a Saccharomyces cerevisiae metabolite. It is a 3beta-sterol, an ergostanoid, a 3beta-hydroxy-Delta(5)-steroid and a member of phytosterols. A steroid of interest both because its biosynthesis in FUNGI is a target of ANTIFUNGAL AGENTS, notably AZOLES, and because when it is present in SKIN of animals, ULTRAVIOLET RAYS break a bond to result in ERGOCALCIFEROL. Ergosterol is a natural product found in Gladiolus italicus, Ramaria formosa, and other organisms with data available. ergosterol is a metabolite found in or produced by Saccharomyces cerevisiae. A steroid occurring in FUNGI. Irradiation with ULTRAVIOLET RAYS results in formation of ERGOCALCIFEROL (vitamin D2). See also: Reishi (part of). Ergosterol, also known as provitamin D2, belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, ergosterol is considered to be a sterol lipid molecule. Ergosterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Ergosterol is the biological precursor to vitamin D2. It is turned into viosterol by ultraviolet light, and is then converted into ergocalciferol, which is a form of vitamin D. Ergosterol is a component of fungal cell membranes, serving the same function that cholesterol serves in animal cells. Ergosterol is not found in mammalian cell membranes. A phytosterol consisting of ergostane having double bonds at the 5,6-, 7,8- and 22,23-positions as well as a 3beta-hydroxy group. Ergosterol. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=57-87-4 (retrieved 2024-07-12) (CAS RN: 57-87-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Ergosterol is the primary sterol found in fungi, with antioxidative, anti-proliferative, and anti-inflammatory effects. Ergosterol is the primary sterol found in fungi, with antioxidative, anti-proliferative, and anti-inflammatory effects.

   

Stearic acid

1-Heptadecanecarboxylic acid

C18H36O2 (284.2715)


Stearic acid, also known as stearate or N-octadecanoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, stearic acid is considered to be a fatty acid lipid molecule. Stearic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Stearic acid can be synthesized from octadecane. Stearic acid is also a parent compound for other transformation products, including but not limited to, 3-oxooctadecanoic acid, (9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoic acid, and 16-methyloctadecanoic acid. Stearic acid can be found in a number of food items such as green bell pepper, common oregano, ucuhuba, and babassu palm, which makes stearic acid a potential biomarker for the consumption of these food products. Stearic acid can be found primarily in most biofluids, including urine, feces, cerebrospinal fluid (CSF), and sweat, as well as throughout most human tissues. Stearic acid exists in all living species, ranging from bacteria to humans. In humans, stearic acid is involved in the plasmalogen synthesis. Stearic acid is also involved in mitochondrial beta-oxidation of long chain saturated fatty acids, which is a metabolic disorder. Moreover, stearic acid is found to be associated with schizophrenia. Stearic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Stearic acid ( STEER-ik, stee-ARR-ik) is a saturated fatty acid with an 18-carbon chain and has the IUPAC name octadecanoic acid. It is a waxy solid and its chemical formula is C17H35CO2H. Its name comes from the Greek word στέαρ "stéar", which means tallow. The salts and esters of stearic acid are called stearates. As its ester, stearic acid is one of the most common saturated fatty acids found in nature following palmitic acid. The triglyceride derived from three molecules of stearic acid is called stearin . Stearic acid, also known as octadecanoic acid or C18:0, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Stearic acid (its ester is called stearate) is a saturated fatty acid that has 18 carbons and is therefore a very hydrophobic molecule that is practically insoluble in water. It exists as a waxy solid. In terms of its biosynthesis, stearic acid is produced from carbohydrates via the fatty acid synthesis machinery wherein acetyl-CoA contributes two-carbon building blocks, up to the 16-carbon palmitate, via the enzyme complex fatty acid synthase (FA synthase), at which point a fatty acid elongase is needed to further lengthen it. After synthesis, there are a variety of reactions it may undergo, including desaturation to oleate via stearoyl-CoA desaturase (PMID: 16477801). Stearic acid is found in all living organisms ranging from bacteria to plants to animals. It is one of the useful types of saturated fatty acids that comes from many animal and vegetable fats and oils. For example, it is a component of cocoa butter and shea butter. It is used as a food additive, in cleaning and personal care products, and in lubricants. Its name comes from the Greek word stear, which means ‚Äòtallow‚Äô or ‚Äòhard fat‚Äô. Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils. Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils.

   

Ergosterol peroxide

5-[(3E)-5,6-dimethylhept-3-en-2-yl]-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-13-ol

C28H44O3 (428.329)


Ergosterol peroxide is found in fruits. Ergosterol peroxide is obtained from leaves of Ananas comosus (pineapple obtained from leaves of Ananas comosus (pineapple). Ergosterol peroxide is found in pineapple and fruits.

   

Ergosterol peroxide

Ergosterol peroxide

C28H44O3 (428.329)


   

Ergosterol

(3S,9S,10R,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol

C28H44O (396.3392)


Indicator of fungal contamination, especies in cereals. Occurs in yeast and fungi. The main fungal steroidand is also found in small amts. in higher plant prods., e.g. palm oil [DFC]. D018977 - Micronutrients > D014815 - Vitamins > D000072664 - Provitamins Disclaimer: While authors make an effort to ensure that the content of this record is accurate, the authors make no representations or warranties in relation to the accuracy or completeness of the record. This record do not reflect any viewpoints of the affiliation and organization to which the authors belong. Ergosterol is the primary sterol found in fungi, with antioxidative, anti-proliferative, and anti-inflammatory effects. Ergosterol is the primary sterol found in fungi, with antioxidative, anti-proliferative, and anti-inflammatory effects.

   

stearic acid

octadecanoic acid

C18H36O2 (284.2715)


Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils. Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils.

   

Octadecanoic acid

Octadecanoic acid

C18H36O2 (284.2715)


A C18 straight-chain saturated fatty acid component of many animal and vegetable lipids. As well as in the diet, it is used in hardening soaps, softening plastics and in making cosmetics, candles and plastics.

   

methyl 7-hydroxy-2,3,3,9-tetramethyl-4,5-dioxo-2h-naphtho[1,2-b]furan-6-carboxylate

methyl 7-hydroxy-2,3,3,9-tetramethyl-4,5-dioxo-2h-naphtho[1,2-b]furan-6-carboxylate

C18H18O6 (330.1103)


   

(4s,10r,11r,15r,18s,20r)-10-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-18,25,34-trihydroxy-11,15,27,27,28-pentamethyl-3,29-dioxa-21-azanonacyclo[22.10.1.0²,²².0⁴,²⁰.0⁶,¹⁴.0⁷,¹¹.0¹⁵,²⁰.0²⁶,³⁰.0³¹,³⁵]pentatriaconta-1(35),2(22),5,24,26(30),31,33-heptaen-23-one

(4s,10r,11r,15r,18s,20r)-10-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-18,25,34-trihydroxy-11,15,27,27,28-pentamethyl-3,29-dioxa-21-azanonacyclo[22.10.1.0²,²².0⁴,²⁰.0⁶,¹⁴.0⁷,¹¹.0¹⁵,²⁰.0²⁶,³⁰.0³¹,³⁵]pentatriaconta-1(35),2(22),5,24,26(30),31,33-heptaen-23-one

C46H59NO6 (721.4342)


   

2-[3-(6-methyldodec-5-en-1-yl)oxiran-2-yl]prop-2-enoic acid

2-[3-(6-methyldodec-5-en-1-yl)oxiran-2-yl]prop-2-enoic acid

C18H30O3 (294.2195)


   

10-(5,6-dimethylhept-3-en-2-yl)-18,25,34-trihydroxy-11,15,27,27,28,32-hexamethyl-3,21,29-trioxanonacyclo[22.10.1.0²,²².0⁴,²⁰.0⁶,¹⁴.0⁷,¹¹.0¹⁵,²⁰.0²⁶,³⁰.0³¹,³⁵]pentatriaconta-1(34),2(22),5,24(35),25,30,32-heptaen-23-one

10-(5,6-dimethylhept-3-en-2-yl)-18,25,34-trihydroxy-11,15,27,27,28,32-hexamethyl-3,21,29-trioxanonacyclo[22.10.1.0²,²².0⁴,²⁰.0⁶,¹⁴.0⁷,¹¹.0¹⁵,²⁰.0²⁶,³⁰.0³¹,³⁵]pentatriaconta-1(34),2(22),5,24(35),25,30,32-heptaen-23-one

C47H60O7 (736.4339)


   

3,7-dihydroxy-1,8,8,9-tetramethyl-9h-phenaleno[1,2-b]furan-4,5,6-trione

3,7-dihydroxy-1,8,8,9-tetramethyl-9h-phenaleno[1,2-b]furan-4,5,6-trione

C19H16O6 (340.0947)


   

(1s,2s,5s,6r,9s,10r,15s)-5-(5,6-dimethylhept-3-en-2-yl)-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-13-ol

(1s,2s,5s,6r,9s,10r,15s)-5-(5,6-dimethylhept-3-en-2-yl)-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-13-ol

C28H44O3 (428.329)


   

(4s,10r,11r,15r,18s,20r)-10-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-18,23,25-trihydroxy-11,15,27,27,28,32-hexamethyl-3,21,29-trioxanonacyclo[22.10.1.0²,²².0⁴,²⁰.0⁶,¹⁴.0⁷,¹¹.0¹⁵,²⁰.0²⁶,³⁰.0³¹,³⁵]pentatriaconta-1,5,22,24,26(30),31(35),32-heptaen-34-one

(4s,10r,11r,15r,18s,20r)-10-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-18,23,25-trihydroxy-11,15,27,27,28,32-hexamethyl-3,21,29-trioxanonacyclo[22.10.1.0²,²².0⁴,²⁰.0⁶,¹⁴.0⁷,¹¹.0¹⁵,²⁰.0²⁶,³⁰.0³¹,³⁵]pentatriaconta-1,5,22,24,26(30),31(35),32-heptaen-34-one

C47H60O7 (736.4339)


   

(4s,10r,11r,15r,18s,20r)-10-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-18,25,34-trihydroxy-11,15,27,27,28,32-hexamethyl-3,21,29-trioxanonacyclo[22.10.1.0²,²².0⁴,²⁰.0⁶,¹⁴.0⁷,¹¹.0¹⁵,²⁰.0²⁶,³⁰.0³¹,³⁵]pentatriaconta-1(34),2(22),5,24(35),25,30,32-heptaen-23-one

(4s,10r,11r,15r,18s,20r)-10-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-18,25,34-trihydroxy-11,15,27,27,28,32-hexamethyl-3,21,29-trioxanonacyclo[22.10.1.0²,²².0⁴,²⁰.0⁶,¹⁴.0⁷,¹¹.0¹⁵,²⁰.0²⁶,³⁰.0³¹,³⁵]pentatriaconta-1(34),2(22),5,24(35),25,30,32-heptaen-23-one

C47H60O7 (736.4339)


   

(9r)-3,7-dihydroxy-1,8,8,9-tetramethyl-5-{[(9r)-3,4,7-trihydroxy-1,8,8,9-tetramethyl-6-oxo-9h-phenaleno[1,2-b]furan-5-yl]imino}-9h-phenaleno[1,2-b]furan-4,6-dione

(9r)-3,7-dihydroxy-1,8,8,9-tetramethyl-5-{[(9r)-3,4,7-trihydroxy-1,8,8,9-tetramethyl-6-oxo-9h-phenaleno[1,2-b]furan-5-yl]imino}-9h-phenaleno[1,2-b]furan-4,6-dione

C38H33NO10 (663.2104)


   

7-hydroxy-2,3,3,9-tetramethyl-2h-naphtho[1,2-b]furan-4,5-dione

7-hydroxy-2,3,3,9-tetramethyl-2h-naphtho[1,2-b]furan-4,5-dione

C16H16O4 (272.1049)


   

(12s)-6,15-dihydroxy-8,12,13,13-tetramethyl-4,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),5,7,9,14-pentaene-2,3-dione

(12s)-6,15-dihydroxy-8,12,13,13-tetramethyl-4,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),5,7,9,14-pentaene-2,3-dione

C18H16O6 (328.0947)


   

2-[(2r,3r)-3-[(5e)-6-methyldodec-5-en-1-yl]oxiran-2-yl]prop-2-enoic acid

2-[(2r,3r)-3-[(5e)-6-methyldodec-5-en-1-yl]oxiran-2-yl]prop-2-enoic acid

C18H30O3 (294.2195)


   

(9r)-4,6,7-trihydroxy-1,8,8,9-tetramethyl-5-{[(9r)-4,6,7-trihydroxy-1,8,8,9-tetramethyl-3-oxo-9h-phenaleno[1,2-b]furan-5-yl]methyl}-9h-phenaleno[1,2-b]furan-3-one

(9r)-4,6,7-trihydroxy-1,8,8,9-tetramethyl-5-{[(9r)-4,6,7-trihydroxy-1,8,8,9-tetramethyl-3-oxo-9h-phenaleno[1,2-b]furan-5-yl]methyl}-9h-phenaleno[1,2-b]furan-3-one

C39H36O10 (664.2308)


   

10-(5,6-dimethylhept-3-en-2-yl)-18,25,34-trihydroxy-11,15,27,27,28-pentamethyl-3,29-dioxa-21-azanonacyclo[22.10.1.0²,²².0⁴,²⁰.0⁶,¹⁴.0⁷,¹¹.0¹⁵,²⁰.0²⁶,³⁰.0³¹,³⁵]pentatriaconta-1(35),2(22),5,24,26(30),31,33-heptaen-23-one

10-(5,6-dimethylhept-3-en-2-yl)-18,25,34-trihydroxy-11,15,27,27,28-pentamethyl-3,29-dioxa-21-azanonacyclo[22.10.1.0²,²².0⁴,²⁰.0⁶,¹⁴.0⁷,¹¹.0¹⁵,²⁰.0²⁶,³⁰.0³¹,³⁵]pentatriaconta-1(35),2(22),5,24,26(30),31,33-heptaen-23-one

C46H59NO6 (721.4342)


   

(12s)-2,4-dihydroxy-8,12,13,13-tetramethyl-3,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1,4,7,9(16),10(14)-pentaene-6,15-dione

(12s)-2,4-dihydroxy-8,12,13,13-tetramethyl-3,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1,4,7,9(16),10(14)-pentaene-6,15-dione

C18H16O6 (328.0947)