Pachymic acid

Pachymic acid
Names

IUPAC name 3-Acetoxy-16-hydroxy-24-methylenelanost-8-en-21-oic acid
Systematic IUPAC name (2R)-2-[(3S,5R,10S,13R,14R,16R,17R)-3-acetyloxy-16-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoic acid
Identifiers
CAS Number	29070-92-6^Y
ChEMBL	ChEMBL468034
ChemSpider	280037^Y
Jmol interactive 3D	Image
KEGG	C17044
PubChem	5484385
InChI InChI=1S/C20H32O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(24-23)17-15-18-20(21)22/h6-7,9-10,12-14,16,19,23H,2-5,8,11,15,17-18H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-14+^Y Key: JNUUNUQHXIOFDA-XTDASVJISA-N^Y InChI=1S/C33H52O5/c1-19(2)20(3)10-11-22(29(36)37)28-25(35)18-33(9)24-12-13-26-30(5,6)27(38-21(4)34)15-16-31(26,7)23(24)14-17-32(28,33)8/h19,22,25-28,35H,3,10-18H2,1-2,4-9H3,(H,36,37)/t22-,25-,26+,27+,28+,31-,32-,33+/m1/s1 Key: VDYCLYGKCGVBHN-DRCQUEPLSA-N
SMILES CC(C)C(=C)CC[C@H]([C@H]1[C@@H](C[C@@]2([C@@]1(CCC3=C2CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)OC(=O)C)C)C)C)O)C(=O)O
Properties
Chemical formula	C₃₃H₅₂O₅
Molar mass	528.76 g/mol
Density	1.1±0.1 g/cm3
Boiling point	612.2±55.0 °C at 760 mmHg
Hazards
Flash point	184.7±25.0 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Pachymic acid is a natural triterpenoid chemical that can be extracted from the root of various Pinus species, where it is produced by parasitic fungus Wolfiporia extensa (synonym Wolfiporia cocos). The dried sclerotia of the fungus is used as a traditional Chinese medicine, and pachymic acid is one of the major bioactive components of it.^[1]

Effects

Pachymic acid is known to inhibit the Epstein-Barr virus and to inhibit the snake venom phospholipase A2.^[2] It also has antitumor and anti-inflammatory properties.^[1]

References

1 2 Shu, Shaohua; Chen, Bei; Zhou, Mengchun; Zhao, Xinmei; Xia, Haiyang; Wang, Mo (2013). "De Novo Sequencing and Transcriptome Analysis of Wolfiporia cocos to Reveal Genes Related to Biosynthesis of Triterpenoids". PLOS ONE 8 (8): e71350. doi:10.1371/journal.pone.0071350. PMC 3743799. PMID 23967197.
↑ "Pachymic acid Biological Test Results". PubChem compound database. 3 March 2016.

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