Bufol

Bufol
Names
	IUPAC name 5α:(3R,5R,7R,8R,9S,10S,12S,13R,14S,17R)-17-[(2R)-6,7-dihydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7,12-triol 5β:(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-17-[(2R)-6,7-dihydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7,12-triol
Identifiers
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:182127 ;
	InChI InChI=1S/C27H48O5/c1-16(6-5-10-25(2,32)15-28)19-7-8-20-24-21(14-23(31)27(19,20)4)26(3)11-9-18(29)12-17(26)13-22(24)30/h16-24,28-32H,5-15H2,1-4H3/t16-,17-,18-,19-,20+,21+,22-,23+,24+,25?,26+,27-/m1/s1 Key: XZDHXPDYLPEFQI-GIQUADRUSA-N;
	SMILES C[C@H](CCCC(C)(CO)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2[C@@H](C[C@@H]4[C@@]3(CC[C@H](C4)O)C)O)O)C;
Identifiers
CAS Number	6127-75-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:194331 ;
	InChI InChI=1S/C27H48O5/c1-16(6-5-10-25(2,32)15-28)19-7-8-20-24-21(14-23(31)27(19,20)4)26(3)11-9-18(29)12-17(26)13-22(24)30/h16-24,28-32H,5-15H2,1-4H3/t16-,17+,18-,19-,20+,21+,22-,23+,24+,25?,26+,27-/m1/s1 Key: XZDHXPDYLPEFQI-FIMPYCPFSA-N;
	SMILES C[C@H](CCCC(C)(CO)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)O)C;
Properties
Chemical formula	C27H48O5
Molar mass	452.676 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Bufol is a steroid and/or 'bile alcohol' found in toads and frogs, which is secreted from the gallbladder of certain species of toads, frogs and other animals. In a broad biological sense, bufol can be classified as a lipid, as it is a polyatomic bile alcohol with a steroidal structure.^[1]^[2]^[3]^[4]^[5]

Natural occurrence

Stereoisomers (5α-bufol and 5β-bufol) were found in the gallbladder of the following amphibians:

5α-bufol: Lepidosiren paradoxa, Neoceratodus forsteri, Ptychadena mascareniensis, Hylarana albolabris, Rana plancyi.^[1]^[3]^[4]^[5]

5β-bufol: Bufo japonicus, Bufo bufo, Rhinella marina, Sclerophrys regularis, Sclerophrys maculata (Bufo maculatus).^[2]^[3]

References

1 2 Une, M.; Matsumoto, N.; Kihira, K.; Yasuhara, M.; Kuramoto, T.; Hoshita, T. (1980). "Bile salts of frogs: a new higher bile acid, 3 alpha, 7 alpha, 12 alpha, 26-tetrahydroxy-5 beta-cholestanoic acid from the bile Rana plancyi". Journal of Lipid Research. 21 (3): 269–276. doi:10.1016/S0022-2275(20)39805-9. ISSN 0022-2275. PMID 7381321.
1 2 Yoshii, M.; Une, M.; Kihira, K.; Kuramoto, T.; Akizawa, T.; Yoshioka, M.; Butler, V. P.; Hoshita, T. (1994). "Bile salts of the toad, Bufo marinus: characterization of a new unsaturated higher bile acid, 3 alpha,7 alpha,12 alpha,26-tetrahydroxy-5 beta-cholest-23-en-27-oic acid". Journal of Lipid Research. 35 (9): 1646–1651. doi:10.1016/S0022-2275(20)41162-9. ISSN 0022-2275. PMID 7806978.
1 2 3 Anderson, I. G.; Haslewood, G. A.; Oldham, R. S.; Amos, B.; Tökés, L. (1974). "A more detailed study of bile salt evolution, including techniques for small-scale identification and their application to amphibian biles". The Biochemical Journal. 141 (2): 485–494. doi:10.1042/bj1410485. ISSN 0264-6021. PMC 1168103. PMID 4218097.
1 2 Amos, B.; Anderson, I. G.; Haslewood, G. A.; Tökes, L. (1977-02-01). "Bile salts of the lungfishes Lepidosiren, Neoceratodus and Protopterus and those of the coelacanth Latimeria chalumnae Smith". The Biochemical Journal. 161 (2): 201–204. doi:10.1042/bj1610201. ISSN 0264-6021. PMC 1164495. PMID 849257.
1 2 Anderson, I. G.; Briggs, T.; Haslewood, G. A.; Oldham, R. S.; Schären, H.; Tökés, L. (1979-12-01). "Comparison of the bile salts of frogs with those of their tadpoles. Bile-salt changes during the metamorphosis of Rana Catesbeiana Shaw". The Biochemical Journal. 183 (3): 507–511. doi:10.1042/bj1830507. ISSN 0264-6021. PMC 1161630. PMID 317247.

[Une-1980-1] 1 2 Une, M.; Matsumoto, N.; Kihira, K.; Yasuhara, M.; Kuramoto, T.; Hoshita, T. (1980). "Bile salts of frogs: a new higher bile acid, 3 alpha, 7 alpha, 12 alpha, 26-tetrahydroxy-5 beta-cholestanoic acid from the bile Rana plancyi". Journal of Lipid Research. 21 (3): 269–276. doi:10.1016/S0022-2275(20)39805-9. ISSN 0022-2275. PMID 7381321.

[Yoshii-1994-2] 1 2 Yoshii, M.; Une, M.; Kihira, K.; Kuramoto, T.; Akizawa, T.; Yoshioka, M.; Butler, V. P.; Hoshita, T. (1994). "Bile salts of the toad, Bufo marinus: characterization of a new unsaturated higher bile acid, 3 alpha,7 alpha,12 alpha,26-tetrahydroxy-5 beta-cholest-23-en-27-oic acid". Journal of Lipid Research. 35 (9): 1646–1651. doi:10.1016/S0022-2275(20)41162-9. ISSN 0022-2275. PMID 7806978.

[Anderson-1974-3] 1 2 3 Anderson, I. G.; Haslewood, G. A.; Oldham, R. S.; Amos, B.; Tökés, L. (1974). "A more detailed study of bile salt evolution, including techniques for small-scale identification and their application to amphibian biles". The Biochemical Journal. 141 (2): 485–494. doi:10.1042/bj1410485. ISSN 0264-6021. PMC 1168103. PMID 4218097.

[Amos-1977-4] 1 2 Amos, B.; Anderson, I. G.; Haslewood, G. A.; Tökes, L. (1977-02-01). "Bile salts of the lungfishes Lepidosiren, Neoceratodus and Protopterus and those of the coelacanth Latimeria chalumnae Smith". The Biochemical Journal. 161 (2): 201–204. doi:10.1042/bj1610201. ISSN 0264-6021. PMC 1164495. PMID 849257.

[Anderson-1979-5] 1 2 Anderson, I. G.; Briggs, T.; Haslewood, G. A.; Oldham, R. S.; Schären, H.; Tökés, L. (1979-12-01). "Comparison of the bile salts of frogs with those of their tadpoles. Bile-salt changes during the metamorphosis of Rana Catesbeiana Shaw". The Biochemical Journal. 183 (3): 507–511. doi:10.1042/bj1830507. ISSN 0264-6021. PMC 1161630. PMID 317247.

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