471-62-5

Basic information

• Product Name: 17BETA(H), 21BETA(H)-HOPANE
• Synonyms: 17BETA(H), 21BETA(H)-HOPANE;17beta(H),21beta(H)-Hopane solution;hopane;Aμ-Neogammacerane;A'-Neo-5α-gammacerane;(3R,3aS,5aR,5bR,7aS,11aS,11bR,13aR,13bS)-3-isopropyl-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysene;(3R,3aS,5aR,5bR,7aS,11aS,11bR,13aR,13bS)-5a,5b,8,8,11a,13b-hexamethyl-3-propan-2-yl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysene;17(H),21(H)-Hopane
• CAS NO: 471-62-5
• Molecular Formula: C30H52
• Molecular Weight: 412.73
• EINECS: 208-759-1
• Mol File: 471-62-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 457.4 °C at 760 mmHg
• Flash Point: -12 °C
• Appearance: /
• Density: 0.925 g/cm³
• Vapor Pressure: 4.06E-08mmHg at 25°C
• Refractive Index: 1.497
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 17BETA(H), 21BETA(H)-HOPANE(CAS DataBase Reference)
• NIST Chemistry Reference: 17BETA(H), 21BETA(H)-HOPANE(471-62-5)
• EPA Substance Registry System: 17BETA(H), 21BETA(H)-HOPANE(471-62-5)

Safety Data

• Hazard Codes: F,Xn,N
• Statements: 11-38-50/53-65-67
• Safety Statements: 60-61-62-33-29-16-9
• RIDADR: UN 1262 3/PG 2
• WGK Germany: 2
• Hazardous Substances Data: 471-62-5(Hazardous Substances Data)

Usage

General Description

17BETA(H), 21BETA(H)-Hopane is a chemical compound often used as a biomarker in the field of geology, specifically in petroleum exploration. Belonging to the hopane family, this pentacyclic compound is derived from a class of biochemicals known as hopanoids, which are produced by certain bacteria. The fossilized remnants of these compounds can often be found in petroleum and other sedimentary rock deposits, helping scientists to determine the age and origin of the deposits. Given their stability and resistance to change over time, these hopanes provide crucial information about the Earth's geological past.

InChI:InChI=1/C30H52/c1-20(2)21-12-17-27(5)22(21)13-18-29(7)24(27)10-11-25-28(6)16-9-15-26(3,4)23(28)14-19-30(25,29)8/h20-25H,9-19H2,1-8H3/t21-,22+,23+,24-,25-,27+,28+,29-,30-/m1/s1

Upstream product

• 863398-02-1 (4S,5R)-4-Benzyloxymethyl-2,2-dimethyl-5-(R)-oxiranyl-[1,3]dioxolane 
• 934356-93-1 1,4-bis-O-benzyl-2,3-O-isopropylidene-5-aldehydo-D-ribitol 
• 934356-90-8 30-phenylthiohopane 
• 155681-03-1 benzyl 2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,4-furanoside 
• 33985-40-9 (3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde 
• 471-62-5 Hopan 
• 38706-33-1 (22S)-hopan-29-ol 

Downstream Products

• 471-62-5 21αH-Hopan 
• 546-99-6 Hop-17⁽²¹⁾-ene 
• 471-62-5 17α,21α-Hopan 
• 132872-64-1 C₃₀H₄₆S 
• 132872-65-2 C₃₀H₄₄S 

Relevant articles and documents

Complex biohopanoids synthesis: Efficient anchoring of ribosyl subunits onto a C30 hopane

Bacteriohopanoids represent a particularly important series of triterpenoids, widely distributed in bacteria. One of the common features of these pentacyclic hopanepolyols is the presence of an extended non-terpenoid and polyhydroxylated side chain attached to the triterpenic moiety through a C-C bond. The biological function of biohopanoids also has to be addressed when one considers the broad diversity in both structures and functionalities found in the side chain. Moreover, the stereochemistries of some biohopanoids are still unconfirmed, due to the lack of synthetic methods to prepare them. In this study we describe an efficient methodology for the formation of the C-C bond between the C30-hopane component and C5-polyhydroxylated carbohydrates through the use of a hopanyllithium intermediate, which has enabled us to synthesize several biohopanoid derivatives. We also report the first synthesis of hopanepentol bearing an additional hydroxy group at position C31.

Bromine, N-bromosuccinimide and sulphur induced isomerizations in the hopane series

When reacted with bromine, N-bromosuccinimide or molten sulphur, triterpenoids of the 17β(H),21β(H)-hopane series were converted into their 17α(H),21β(H) and 17β(H),21α(H) isomers of geochemical significance.