175205-40-0

Basic information

• Product Name: 17-(1,5-DIMETHYLHEX-4-ENYL)-4,4,10,14-TETRAMETHYL-2,3,4,5,6,7,10,11,12,13,14,15,16,17-TETRADECAHYDRO-1H-CYCLOPENTA[A]PHENANTHREN-3-OL
• Synonyms: 17-(1,5-DIMETHYLHEX-4-ENYL)-4,4,10,14-TETRAMETHYL-2,3,4,5,6,7,10,11,12,13,14,15,16,17-TETRADECAHYDRO-1H-CYCLOPENTA[A]PHENANTHREN-3-OL;17-(1,5-Dimethylhex-4-enyl)-4,4,10,14-tetramethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phe;LANOSTEROL(3/3-HYDROXY-8,24-IANOSTADIENE)
• CAS NO: 175205-40-0
• Molecular Formula: C29H48O
• Molecular Weight: 412.69
• Mol File: 175205-40-0.mol

Chemical Properties

• Boiling Point: 495.1°Cat760mmHg
• Flash Point: 217.7°C
• Appearance: /
• Density: 0.99g/cm³
• Vapor Pressure: 7.07E-12mmHg at 25°C
• Refractive Index: 1.531
• CAS DataBase Reference: 17-(1,5-DIMETHYLHEX-4-ENYL)-4,4,10,14-TETRAMETHYL-2,3,4,5,6,7,10,11,12,13,14,15,16,17-TETRADECAHYDRO-1H-CYCLOPENTA[A]PHENANTHREN-3-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 17-(1,5-DIMETHYLHEX-4-ENYL)-4,4,10,14-TETRAMETHYL-2,3,4,5,6,7,10,11,12,13,14,15,16,17-TETRADECAHYDRO-1H-CYCLOPENTA[A]PHENANTHREN-3-OL(175205-40-0)
• EPA Substance Registry System: 17-(1,5-DIMETHYLHEX-4-ENYL)-4,4,10,14-TETRAMETHYL-2,3,4,5,6,7,10,11,12,13,14,15,16,17-TETRADECAHYDRO-1H-CYCLOPENTA[A]PHENANTHREN-3-OL(175205-40-0)

Safety Data

• Hazardous Substances Data: 175205-40-0(Hazardous Substances Data)

Usage

Classification

Cyclopentaphenanthrene

Explanation

The compound belongs to the class of cyclopentaphenanthrene, which are organic compounds containing a cyclopentane ring fused to a phenanthrene ring system.

Explanation

Sterol is a subgroup of steroids that includes compounds with a hydroxyl group, and steroid hormones are a class of hormones that are derived from this group.

Explanation

The compound has a cyclopentane ring system, which is a five-membered carbon ring, and a side chain consisting of various methyl groups and a 1,5-dimethylhex-4-enyl group.

Explanation

The side chain of the compound is a 1,5-dimethylhex-4-enyl group, which is a branched chain with two methyl groups and a double bond at the 4th position.

Explanation

The compound can serve as a precursor for the synthesis of other important compounds, such as hormones and signaling molecules, which are crucial for various biological functions and processes.

Explanation

The compound has a tetradecahydro (14 hydrogen atoms) framework, which means it has 14 hydrogen atoms added to the carbon skeleton, making it a saturated hydrocarbon.

Explanation

The compound has a hydroxyl group attached to the carbon skeleton, which is a key functional group that contributes to its classification as a sterol and its potential biological activities.

Explanation

The molecular formula represents the total number of carbon (C), hydrogen (H), and oxygen (O) atoms in the compound, which is 30 carbon atoms, 50 hydrogen atoms, and 1 oxygen atom.

Type

Sterol and steroid hormone

Structure

Cyclopentane ring system and a side chain

Methyl groups

Four methyl groups at positions 4, 4, 10, and 14

Side chain

1,5-dimethylhex-4-enyl group

Natural occurrence

Found in plants and animals

Biological activities

Precursor for synthesis of hormones and signaling molecules

Hydrocarbon framework

Tetradecahydro

Functional group

Hydroxyl group (-OH)

InChI:InChI=1/C29H48O/c1-19(2)9-8-10-20(3)21-15-17-28(6)22(21)11-12-24-23(28)13-14-25-27(4,5)26(30)16-18-29(24,25)7/h9,20-22,25-26,30H,8,10-18H2,1-7H3

Upstream product

• 1417697-31-4 (2E,6E,10E)-14-bromo-7,11,15-trimethylhexadeca-2,6,10-triene-1,15-diol 
• 1417697-32-5 (6E,10E,14E)-3,16-dibromo-2,6,10-trimethylhexadeca-6,10,14-trien-2-ol 
• 1417697-33-6 C₃₅H₅₂O₃S 
• 19902-79-5 28-noroxidosqualene 
• 67858-78-0 (4E, 8E)-5,9,13-trimethyl-4,8,12-tetradecatrienal 
• 67858-73-5 (2E,6E,10E)-7,11,15-trimethylhexadeca-2,6,10,14-tetraen-1-ol 

Relevant articles and documents

Lanosterol biosynthesis: The critical role of the methyl-29 group of 2,3-oxidosqualene for the correct folding of this substrate and for the construction of the five-membered D ring

Lanosterol synthase catalyzes the polycyclization reaction of (3S)-2,3-oxidosqualene (1) into tetracyclic lanosterol 2 by folding 1 in a chair-boat-chair-chair conformation. 27-Nor- and 29-noroxidosqaulenes (7 and 8, respectively) were incubated with this enzyme to investigate the role of the methyl groups on 1 for the polycyclization cascade. Compound 7 afforded two enzymatic products, namely, 30-norlanosterol (12) and 26-normalabaricatriene (13; 12/13 9:1), which were produced through the normal chair-boat-chair-chair conformation and an atypical chair-chair-boat conformation, respectively. Compound 8 gave two products 14 and 15 (14/15 4:5), which were generated by the normal and the unusual polycyclization pathways through a chair-chair-boat-chair conformation, respectively. It is remarkable that the twist-boat structure for the B-ring formation was changed to an energetically favored chair structure for the generation of 15. Surprisingly, 14 and 15 consisted of a novel 6,6,6,6-fused tetracyclic ring system, thus differing from the 6,6,6,5-fused lanosterol skeleton. Together with previous results, we conclude that the methyl-29 group is critical to the correct folding of 1, with lesser contributions from the other branched methyl groups, such as methyl-26, -27, and -28. Furthermore, we demonstrate that the methyl-29 group has a crucial role in the formation of the five-membered D ring of the lanosterol scaffold. Ringing in the changes: The incubation of 1 with porcine-liver cyclase afforded new nortriterpenes 2 and 3 with 6,6,6,6-fused tetracyclic skeletons, which were produced by chair-boat-chair-chair and chair-chair-boat-chair conformations, respectively (see scheme), thus indicating that the 29-methyl group is critical to the correct folding of oxidosqualene and to the formation of the five-membered D ring for lanosterol biosynthesis. Copyright