Geranic acid - Moligand™,≥85%,mixture of isomers , CAS No.459-80-3

CAS: 459-80-3 Cat. No.: G170455 Molecular Weight: 168.23 Beilstein Registry Number: 1763800 EC Number: 207-299-9

GRADE & PURITY Moligand™, ≥85%, mixture of isomers

Synonyms

DTXCID8027115 | HMS2269B05 | 2,6-OCTADIENOIC ACID, 3,7-DIMETHYL-, (E)- | Geranic acid, (2E)- | EINECS 207-299-9 | Geranilyc acid | 3,7-Dimethyl-2,6(and 2,7)-octadienoic acid | Decaprenoic acid | MFCD20542837 | CAS-459-80-3 | EN300-761337 | 3,7-Dimethyloct

Storage

Room temperature

Shipped In

Normal

Overview

anic acid is a monoterpenemainly used in flavor, fragrance, cosmetics and agro-industries. In vitro studies show that geranic acid exhibits strong inhibitory activity against Fusarium graminearum and Colletotrichum graminicola, the two main fungal pathogens of maize. It may be responsible for the potent tyrosinase inhibitory activity of lemongrass (Cymbopogon citratus).

Specifications

Synonyms

DTXCID8027115 | HMS2269B05 | 2, 6-OCTADIENOIC ACID, 3, 7-DIMETHYL-, (E)- | Geranic acid, (2E)- | EINECS 207-299-9 | Geranilyc acid | 3, 7-Dimethyl-2, 6(and 2, 7)-octadienoic acid | Decaprenoic acid | MFCD20542837 | CAS-459-80-3 | EN300-761337 | 3, 7-Dimethyloct

Specifications & Purity

Moligand™, ≥85%, mixture of isomers

Biochemical and Physiological Mechanisms

Smell (pure): sweet, green flowers, like geranium leaves, wood, citrus, 20ppm: sweet, wood, leaves, fruit, with a slight aftertaste.

Storage

Room temperature

Shipped In

Normal

Grade

Moligand™

Purity

≥85%

Names and Identifiers

• Pubchem Sid: 488195198
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488195198
• Canonical Smiles: CC(=CCCC(=CC(=O)O)C)C
• IUPAC Name: (2E)-3,7-dimethylocta-2,6-dienoic acid
• InChIKey: ZHYZQXUYZJNEHD-VQHVLOKHSA-N
• INCHI: 1S/C10H16O2/c1-8(2)5-4-6-9(3)7-10(11)12/h5,7H,4,6H2,1-3H3,(H,11,12)/b9-7+
• Isomeric SMILES: CC(=CCC/C(=C/C(=O)O)/C)C
• WGK Germany: 3
• RTECS: RG5380000
• Molecular Weight: 168.23
• Beilstein: 1763800
• Reaxy-Rn: 1763804
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1763804&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Monoterpenoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Monoterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Acyclic monoterpenoids
• Alternative Parents: Medium-chain fatty acids Methyl-branched fatty acids Unsaturated fatty acids Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Acyclic monoterpenoid - Medium-chain fatty acid - Branched fatty acid - Methyl-branched fatty acid - Unsaturated fatty acid - Fatty acyl - Fatty acid - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organooxygen compound - Carbonyl group - Hydrocarbon derivative - Organic oxide - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.
• External Descriptors: Unsaturated fatty acids

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

ATM Tchem Serine-protein kinase ATM (4198 Activities)

Discover Target: ATM

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GNAS Tbio Guanine nucleotide-binding protein G(s), subunit alpha (103405 Activities)

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POLI Tchem DNA polymerase iota (116820 Activities)

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KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)

Discover Target: KDM4E

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Associated Targets(non-human)

Pseudomonas aeruginosa (123386 Activities)

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Staphylococcus aureus (210822 Activities)

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Staphylococcus epidermidis (22802 Activities)

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Escherichia coli (133304 Activities)

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Enterococcus hirae (484 Activities)

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Plasmodium falciparum (966862 Activities)

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Candida albicans (78123 Activities)

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TGR Thioredoxin glutathione reductase (28579 Activities)

Discover Target: TGR

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: solubility H2O: insoluble alcohol: soluble
• Refractive Index: 1.484 (lit.
• Flash Point(°F): 271.4 °F
• Flash Point(°C): 133 °C
• Boil Point(°C): 250°C
• Molecular Weight: 168.230 g/mol
• XLogP3: 3.100
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 168.115 Da
• Monoisotopic Mass: 168.115 Da
• Topological Polar Surface Area: 37.300 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 208.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

References

1. Junyao Li, Changhong Hao, Huiyan Jia, Jing Zhang, Huiting Wu, Jingming Ning, Rangjian Wang, Wei-Wei Deng.  (2022)  Aroma characterization and their changes during the processing of black teas from the cultivar, Camellia sinensis (L.) O. Kuntze cv. Jinmudan.  JOURNAL OF FOOD COMPOSITION AND ANALYSIS,      [PMID:] [10.1016/j.jfca.2022.104449]

2. Wei Zhan, Chao Yuan, Bo Cui, Bin Yu, Pengfei Liu, Zhengzong Wu, Haibo Zhao.  (2021)  Effect of chain length on the structure and physicochemical properties of active compound/linear dextrin composites.  CARBOHYDRATE POLYMERS,      [PMID:34294321] [10.1016/j.carbpol.2021.118304]