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Chemistry

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Also known as: 738-87-4, Sterculinic acid, 8-(2-octylcyclopropen-1-yl)octanoic acid, 9,10-methylene-9-octadecenoic acid, Mxv06g5rok, 1-cyclopropene-1-octanoicacid, 2-octyl-
Molecular Formula
C19H34O2
Molecular Weight
294.5  g/mol
InChI Key
PQRKPYLNZGDCFH-UHFFFAOYSA-N
FDA UNII
MXV06G5ROK

Sterculic Acid
sterculic acid is a natural product found in Hibiscus syriacus, Amaranthus cruentus, and other organisms with data available.
1 2D Structure

Sterculic Acid

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
8-(2-octylcyclopropen-1-yl)octanoic acid
2.1.2 InChI
InChI=1S/C19H34O2/c1-2-3-4-5-7-10-13-17-16-18(17)14-11-8-6-9-12-15-19(20)21/h2-16H2,1H3,(H,20,21)
2.1.3 InChI Key
PQRKPYLNZGDCFH-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCCCCCCCC1=C(C1)CCCCCCCC(=O)O
2.2 Other Identifiers
2.2.1 UNII
MXV06G5ROK
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 738-87-4

2. Sterculinic Acid

3. 8-(2-octylcyclopropen-1-yl)octanoic Acid

4. 9,10-methylene-9-octadecenoic Acid

5. Mxv06g5rok

6. 1-cyclopropene-1-octanoicacid, 2-octyl-

7. 1-cyclopropene-1-octanoic Acid, 2-octyl-

8. Omega-(2-n-octylcycloprop-1-enyl)octanoic Acid

9. 2-octyl-1-cyclopropene-1-octanoic Acid

10. Sterculia-saeure

11. Unii-mxv06g5rok

12. Sterculinsaeure

13. Stearculic Acid

14. Ster-culic Acid

15. Stearculinic Acid

16. Hsdb 3904

17. Schembl31295

18. 2-octyl-1-cyclopropene-1-octanoic Acid Homopolymer

19. 55088-60-3

20. Sterculic Acid [hsdb]

21. Chebi:9261

22. Us8962837, Sterculic Acid

23. 1-cyclopropene-1-octanoic Acid, 2-octyl-, Homopolymer

24. Chembl3677268

25. Dtxsid90970445

26. Bdbm149345

27. Zinc8221051

28. Lmfa01140018

29. 9,10-mt 9c-18:1

30. 1-cyclopropene-1-octanoic Acid 2-octyl-

31. Da-03178

32. Fa(19:2)

33. 8-(2-octyl-1-cyclopropenyl)octanoic Acid

34. 8-(2-octyl-cycloprop-1-enyl)-octansaeure

35. Hy-127143

36. Cs-0093556

37. Ft-0724977

38. 8-(2-octylcycloprop-1-en-1-yl)octanoic Acid

39. C08366

40. 738s874

41. A837950

42. Q2345401

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 294.5 g/mol
Molecular Formula C19H34O2
XLogP35.8
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count15
Exact Mass294.255880323 g/mol
Monoisotopic Mass294.255880323 g/mol
Topological Polar Surface Area37.3 Ų
Heavy Atom Count21
Formal Charge0
Complexity318
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 Absorption, Distribution and Excretion

STERCULIC ACID IS A NATURALLY OCCURRING CYCLOPROPENOID FATTY ACID. THE DISTRIBUTION OF RADIOACTIVITY FROM STERCULIC ACID, LABELED ON 9,10-METHYLENE C OF THE CYCLOPROPENE RING, WAS INVESTIGATED IN TROUT, S GAIRDNERI. OF THE ADMIN DOSE, 50% WAS EXCRETED IN FECES & URINE BY 168 HR, BUT LESS THAN 1% OF THE DOSE WAS EXPIRED AS CO2 DURING THE SAME TIME PERIOD. INCORPORATION OF RADIOACTIVITY INTO MOST ORGANS PEAKED AT 119 HR & THE MAJORITY OF THE LABEL IN THE LIVER WAS IN THE FATTY ACID PORTION OF THE LIPID FRACTION. RAINBOW TROUT READILY ABSORB, TRANSPORT & INCORPORATE STERCULIC ACID INTO TISSUE LIPID, INCL MEMBRANE LIPID, BUT CANNOT OXIDIZE THE METHYLENE C OF THE CYCLOPROPENOID TO CO2.

EISELE TA ET AL; INCORPORATION OF LABEL FROM (9,10-METHYLENE-14C) STERCULIC ACID IN RAINBOW TROUT, SALMO GAIRDNERI; LIPIDS 14(6) 523 (1979)


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