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Sterculic Acid

Sterculic Acid

Synopsis, 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 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 Formula	C₁₉H₃₄O₂
Molecular Weight	294.5 g/mol
XLogP3	5.8
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	15
Exact Mass	294.255880323 g/mol
Monoisotopic Mass	294.255880323 g/mol
Topological Polar Surface Area	37.3 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	318
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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)