{{위키데이터 속성 추적}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477867469
| Name = 송라산
| ImageFile = Usnic acid.svg
| ImageName = Chemical structure of usnic acid
| IUPACName = 2,6-Diacetyl-7,9-dihydroxy-8,9b-dimethyldibenzo[''b'',''d'']furan-1,3(2''H'',9b''H'')-dione
| OtherNames = {{bulletedlist|Usneine|Usninic acid|Usniacin}}
|Section1={{Chembox Identifiers
| CASNo_Ref =<ref name="AshAsh2004"/>
| CASNo = 125-46-2
| CASNo_Comment = [[racemic]]
| CASNo1 = 7562-61-0
| CASNo1_Comment = (''R'')-(+)
| CASNo2 = 6159-66-6
| CASNo2_Comment = (''S'')-(–)
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 242022
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 38319
| SMILES = CC1=C(C(=C2C(=C1O)C3(C(=CC(=O)C(C3=O)C(=O)C)O2)C)C(=O)C)O
| PubChem = 5646
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5444
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = 0W584PFJ77
| InChI = 1/C18H16O7/c1-6-14(22)12(8(3)20)16-13(15(6)23)18(4)10(25-16)5-9(21)11(7(2)19)17(18)24/h5,11,22-23H,1-4H3
| InChIKey = CUCUKLJLRRAKFN-UHFFFAOYAS
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C18H16O7/c1-6-14(22)12(8(3)20)16-13(15(6)23)18(4)10(25-16)5-9(21)11(7(2)19)17(18)24/h5,11,22-23H,1-4H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = CUCUKLJLRRAKFN-UHFFFAOYSA-N
  }}
|Section2={{Chembox Properties
| C=18 | H=16 | O=7
| Density =
| MeltingPtC = 204
| BoilingPt = 
 }}
}}
'''송라산'''(松蘿酸) 또는 '''우슨산'''({{llang|en|usnic acid}})은 [[송라속]], [[꽃이끼속]], [[아시아노란속매화나무지의속]], [[주황접시지의속]], [[탱자나무지의속]], [[메아리김지의속]], [[매화나무지의속]], [[가시끈지의속]] 등의 [[지의류]]에서 추출되는 [[디벤조푸란]] 유도체로 화학식은 C<sub>18</sub>H<sub>16</sub>O<sub>7</sub>이다. 1844년 독일 과학자 [[빌헬름 크노프]]가 처음으로 분리해냈고,<ref>{{저널 인용| 이탤릭체=예|  last1 = Knop | first1 = W | year = 1844 | title = Chemisch-physiologische Untersuchung uber die Flechten | url = https://zenodo.org/record/1426980| journal = Annalen der Chemie und Pharmacie| volume = 49 | issue = 2| pages = 103–124 | doi=10.1002/jlac.18440490202}}</ref> 1930년대에 [[프랭크 쿠르드]]와 [[알렉산더 로버트슨]]이 인공적으로 합성해냈다.<ref>{{저널 인용| last1 = Robertson | first1 = A. | last2 = Curd | first2 = F. H. | year = 1933 | title =  277. Usnic acid. Part III. Usnetol, usnetic acid, and pyrousnic acid| url = | journal = Journal of the Chemical Society (Resumed)| volume = | issue = | page = 1173 | doi = 10.1039/jr9330001173 |이탤릭체=예 }}</ref> 일반적으로 지의류에서만 발견된다고 생각되지만, [[홍다균]]이나 지의가 아닌 [[자낭균문|자낭균]]에서 발견되는 극소수 사례가 있다.<ref name="CocchiettoSkert2002">{{저널 인용|last1=Cocchietto|first1=Moreno|last2=Skert|first2=Nicola|last3=Nimis|first3=Pier|last4=Sava|first4=Gianni|title=A review on usnic acid, an interesting natural compound|journal=Naturwissenschaften|volume=89|issue=4|year=2002|pages=137–146|issn=0028-1042|doi=10.1007/s00114-002-0305-3|bibcode=2002NW.....89..137C |이탤릭체=예}}</ref><ref name="Blanc1996">{{저널 인용|last1=Blanc|first1=Philippe J.|title=Characterization of the tea fungus metabolites|journal=Biotechnology Letters|volume=18|issue=2|year=1996|pages=139–142|issn=0141-5492|doi=10.1007/BF00128667 |이탤릭체=예}}</ref>

상온에서 쓴맛이 나는 노란색 고체로 존재한다.<ref name="AshAsh2004">{{서적 인용
| author1 =Michael Ash
| author2 =Irene Ash
| title =Handbook of preservatives
| url =https://books.google.com/books?id=XZ2QB7bu5LwC&pg=PA670
| accessdate =5 August 2010
| year =2004
| publisher =Synapse Info Resources
| isbn =978-1-890595-66-1
| page =5856 |이탤릭체=예}}</ref> 송라산의 [[염]]은 '''송라산염'''(松蘿酸鹽, {{llang|en|usnate}})이라고 한다. 송라산은 지의류의 [[2차 대사산물]]로서, 그 역할은 아직 명확하게 규명되지 않았다. 송라산과 송라산염은 특유의 [[간독성]]을 가지고 있으며 [[간부전]]의 원인이 된다.<ref>{{저널 인용|이탤릭체=예 | doi = 10.1111/j.1440-1746.2008.05310.x | pmid = 18318821 | title = Hepatotoxic slimming aids and other herbal hepatotoxins | journal = Journal of Gastroenterology and Hepatology | volume = 23 | issue = 3 | pages = 366–373 | year = 2008 | last1 = Chitturi | first1 = Shivakumar | last2 = Farrell | first2 = Geoffrey C. }}
</ref><ref>{{저널 인용|이탤릭체 = 예
| vauthors = Yellapu RK, Mittal V, Grewal P, Fiel M, Schiano T
| title = Acute liver failure caused by 'fat burners' and dietary supplements: a case report and literature review
| journal = Canadian Journal of Gastroenterology| volume = 25
| issue = 3
| pages = 157–60
| year = 2011
| pmid = 21499580
| pmc = 3076034
| doi = 10.1155/2011/174978
| url = 
}}</ref> 하루에 300–1350 밀리그램을 일주일 동안 경구투여한 결과 다수의 피험자에게서 심각한 간독성이 나타났다.<ref>{{저널 인용|이탤릭체=예 | last1 = Hsu | first1 = LM | last2 = Huang | first2 = YS | last3 = Chang | first3 = FY | last4 = Lee | first4 = SD | date = Jul 2005 | title = 'Fat burner' herb, usnic acid, induced acute hepatitis in a family | url = | journal = Journal of Gastroenterology and Hepatology| volume = 20 | issue = 7| pages = 1138–9 | doi=10.1111/j.1440-1746.2005.03855.x| pmid = 15955234 }}</ref><ref>{{저널 인용| doi = 10.4065/81.4.541 | pmid = 16610575 | title = Severe Hepatotoxicity Associated with Use of a Dietary Supplement Containing Usnic Acid | journal = Mayo Clinic Proceedings | volume = 81 | issue = 4 | pages = 541–544 | year = 2006 | last1 = Sanchez | first1 = William | last2 = Maple | first2 = John T. | last3 = Burgart | first3 = Lawrence J. | last4 = Kamath | first4 = Patrick S. |이탤릭체=예 }}</ref>

== 각주 ==
{{각주}}

== 외부 링크 ==
* {{위키공용분류-줄}}

{{토막글|생물학}}

[[분류:케톤]]
[[분류:유기산]]
[[분류:폴리페놀]]
[[분류:폴리케타이드]]
[[분류:레조르시놀]]
[[분류:다이벤조퓨란]]