Basic information
- CAS
503-05-9- Standard SMILES
CCCCCCCCC1=C(CCCCCCC(=O)O)C1- InChIKey
HPSSZFFAYWBIPY-UHFFFAOYSA-N- Molecular formula
- C18H32O2
- Average molar mass
- 280.4 g/mol
- Monoisotopic mass
- 280.24023026
Overview
Malvalic acid is a long-chain cyclopropenyl fatty acid comprising 8-heptadecenoic acid having a cyclopropene ring arising from the linking of C-8 and C-9 by a methylene substituent. It is a long-chain fatty acid, a cyclopropenyl fatty acid and a monounsaturated fatty acid.
Names & identifiers
- Preferred name
- Malvalic acid
- IUPAC
- 7-(2-octylcyclopropen-1-yl)heptanoic acid
- English name
- malvalic acid
- Molecular formula
- C18H32O2
- Molecular weight
- 280.45
Names & synonyms
MALVALIC ACIDMalvic acid503-05-9Halphen acid7-(2-octylcyclopropen-1-yl)heptanoic acid02AJQ7VS2H8,9-methylene-8Z-heptadecenoic acid2-Octyl-1-cyclopropene-1-heptanoic acid1-Cyclopropene-1-heptanoic acid, 2-octyl-CHEBI:6673DTXSID50198300RefChem:155500
Show more names
Malvalic Acid Sodium Salt
DTXCID401207917-(2-octylcycloprop-1-en-1-yl)heptanoic acid1-Cyclopropene-1-heptanoicacid, 2-octyl-UNII-02AJQ7VS2HMalvalsaeureHSDB 3905SCHEMBL25251MALVALIC ACID [HSDB]
Database identifiers
- CAS
503-05-9- PubChem CID
- 10416
- DTXSID
DTXSID50198300- ChEBI
CHEBI:6673- UNII
- 02AJQ7VS2H
- Nikkaji
- J11.821D
Properties
Computed structural properties
- XLogP
- 6.2
- Topological polar surface area
- 37.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 14
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 305
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Organic Acids
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Carbocyclic fatty acids [FA0114]
Physicochemical properties
- FDA UNII
- 2 AJQ7VS2H · 02AJQ7VS2H
- Hazardous Substances Data
- 503 · 503-05-9(Hazardous Substances Data)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Hazards SummaryMalvalic and sterculic acid are the primary cyclopropenoid fatty acids (CPRAs) in cottonseed oil; They are synergistic with aflatoxin B1, producing hepatic carcinoma in rainbow trout; [HSDB]
Special Reports
THE ROLE OF DIET & NUTRITION IN MODIFYING TUMOR INDUCTION BY CHEMICAL CARCINOGENS IN FOODS & FEEDS IS REVIEWED. FOOD CONTAMINANTS OF MAJOR CONCERN INCLUDE STERCULIC ACID & MALVALIC ACID.[PETERING HG; DIET, NUTRITION, AND CANCER; ADV EXP MED BIOL 91: 207 (1977)]
Toxicology
Interactions
RAINBOW TROUT FED A DIET CONTAINING 200 PPM OF STERCULIC ACID & MALVALIC ACID, SUBSTANCES THAT GREATLY INCR THE SENSITIVITY OF TROUT LIVER CELLS TO CARCINOGENIC EFFECTS OF AFLATOXIN B1. AFTER 4 WK, PECULIAR CLEFT-LIKE STRIATIONS APPEARED IN CYTOPLASM OF HEPATOCYTES. THESE ALTERATIONS BECAME PROGRESSIVELY MORE FREQUENT & MARKED WITH CONTINUED FEEDING OF DIET. AT 8 & 12 WK, ROUGH-SURFACED ENDOPLASMIC RETICULUM CONTAINED MANY PARALLEL ARRAYS & WHORLED PROFILES OF MEMBRANE MATERIAL. GLUCOSE-6-PHOSPHATASE ACTIVITY IN LIVER WAS SIGNIFICANTLY DECREASED.
Safety data
- Hazardous Substances Data
- 503-05-9(Hazardous Substances Data)
Chemistry & industry
Uses & manufacturing
General Manufacturing Information
CYCLOPROPENOID FATTY ACIDS (CPFA), NATURALLY PRESENT IN COTTONSEED OIL, ARE CARCINOGENS & EXHIBIT A POTENT SYNERGISTIC EFFECT ON AFLATOXIN B1 HEPATOCARCINOGENESIS IN RAINBOW TROUT. THE PREDOMINANT CPFA CONSTITUENTS OF COTTONSEED OIL ARE MALVALIC & STERCULIC ACID.
MALAYSIAN KAPOK (C PENTANDRA) SEEDS CONTAIN ABOUT 28% OIL. THE OIL FROM BOTH RAW & ROASTED SEEDS PRODUCED A POSITIVE HALPHEN TEST FOR CYCLOPROPENOID FATTY ACIDS. ACID VALUE, FATTY ACID COMPOSITION BY GLC, I VALUE, REFRACTIVE INDEX, SAPONIFICATION NUMBER, & UNSAPONIFIABLES OF THE OIL WERE ALSO DETERMINED. THE VALUES (AREA %) FOR FATTY ACIDS AS METHYL ESTERS WERE: MALVALIC ACID (7.18%), C22:0 (0.44%) & STERCULIC ACID (2.96%). MALVALIC & STERCULIC ACIDS WERE DETERMINED AS SILVER NITRATE-METHANOL DERIVATIVES OF THEIR METHYL ESTERS.
Upstream & downstream products
Upstream raw materials
Suppliers2 total
河南天孚化工有限公司+86-0371-55170693 +86-19937530512 · [email protected]
TLC梯尔希（南京）药物研发有限公司18012923235 · [email protected]
Additional notes
DefinitionChEBI: A long-chain cyclopropenyl fatty acid comprising 8-heptadecenoic acid having a cyclopropene ring arising from the linking of C-8 and C-9 by a methylene substituent.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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