TIGLIC ACID

PRODUCT IDENTIFICATION

CAS NO. 80-59-1

TIGLIC ACID

EINECS NO. 201-295-0
FORMULA CH3CH=C(CH3)COOH
MOL WT. 100.12

H.S. CODE

2916.19.3000

TOXICITY

Rat LD50 (Oral): > 5gm/kg
SYNONYMS trans-2-Methyl crotonic acid;  Cevadic acid;

(E)-2,3-Dimethylacrylic acid; (E)-2-Methyl-2-butenoic acid; trans-2-Methyl crotonic acid; (E)-2-Methylbut-2-enoic acid; (E)-2-Methylbut-2-ensä ure (German); á cido (E)-2-metilbut-2-enoico (Spanish); Acide (E)-2-mé thylbut-2-é noï que (French); alpha-Methylcrotonic Acid; trans-2,3-Dimethylacrylic acid; Tiglinic acid; trans-2-Methyl-2-butenoic acid; trans-alpha,beta-Dimethylacrylic acid;

SMILES

C(\C(O)=O)(=C\C)C

CLASSIFICATION

Unsaturated Carboxylic Acid, Flavors and Fragrances, Biochemical ex Plants

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE white crystals

MELTING POINT

61 - 65 C
BOILING POINT 198 - 199 C
SPECIFIC GRAVITY 0.969

SOLUBILITY IN WATER

soluble in hot water (1.85E+04 mg/l at 25 C)
VAPOR DENSITY  
pKa 4.96 (Dissociation Constant at 20 C)
log Pow 1.4 (Octanol-water)
VAPOR PRESSURE 0.133 (mmHg at 25 C)
HENRY'S LAW 7.09E-07 (atm-m3/mole at 25 C)
OH RATE 3.12E-11 (cm3/molecule-sec at 25 C Atmospheric )

AUTOIGNITION

 

NFPA RATINGS

Health: 2 Flammability: 0 Reactivity: 0

REFRACTIVE INDEX

 
FLASH POINT

 

STABILITY Stable under ordinary conditions

APPLICATIONS

Crotonic acid is a member of short and unsaturated chain carboxylic acids trans-2-butenoic acid in IUPAC sysytem name and 3-methylacrylic acid in acrylic acid series naming. It is a white to off-white crystals soluble in water (the solution is a weak acid) melting at 71 C boiling at 185 C. It reacts violently with bases, oxidants, reducing agents. It is found in croton oil used as a standard irritant in pharmacological research laxative and poisonous to human. Tiglic acid is structurally the trans- form of methyl branched crotonic acid found in croton oil (trans-2,3-Dimethylacrylic acid in acrylic acid series naming). The cis- form of methyl branched crotonic acid is called angelic acid obtainable naturally from roots of Angelica plant. They are onoclinic poisonous crystals soluble in hot water. They have a reactive solid bond and carboxylic group in one molecule. They can be used as co-monomers for polymerization to prepare functional polymers as well as in protein sequencing and enzyme inhibiting. Their derivatives, acyl halides, anhydrides, esters, amides and nitriles, are used in making target products such as flavoring agents, internal plasticizers, pesticides, dyes, textile treatment agents, fungicides, and pharmaceuticals through further reactions of substitution, catalytic reduction, metal hydride reduction, diborane reduction, keto formation with organometallic reagents, electrophile bonding at oxygen, and Claisen condensation on carboxylic group and electrophilic additions, reduction, oxidation, radical additions,  substitution and dienes formation on solid bond.

Wikipedia Linking: http://en.wikipedia.org/wiki/Tiglic_acid

http://www.unitedteasofwellness.com/
German chamomile is often used topically in a cream or ointment to soothe irritated skin, because of its antibacterial, antifungal, and antiviral properties. Evidence suggests that it may be moderately effective in the treatment of eczema. The essential oil of Roman chamomile consists chiefly of chamazulene, angelic acid, tiglic acid, and several sesquiterpene lactones. Other constituents of Roman chamomile include anthemic acid, athesterol, anthemene, resin and tannin. The essential oil of German chamomile contains chamazulene, -bisabolol, -bisabololaxides A and B, spathulenol cis-En-yn-dicycloether and farnesene. Other constituents of German chamomile include a volatile oil, anthemic acid, antheminidine, tannin, matricarin, and apigenin

http://harker.chem.buffalo.edu/
Single-crystal-to-single-crystal E ! Z isomerization of tiglic acid in a supramolecular framework

http://molecules.gnu-darwin.org/mod/tiglate-more.html
tiglate Molecules Structural Archive and Gallery

SALES SPECIFICATION

APPEARANCE

white crystals
ASSAY

97.5% min

MELTING POINT

61 - 65 C
TRANSPORTATION
PACKING 25kgs in Drum
HAZARD CLASS 8( Packing Group: II)
UN NO. 3261
OTHER INFORMATION
Hazard Symbols: C, Risk Phrases: 34, Safety Phrases: 26-36/37/39-45

UNSATURATED ALIPHATIC CARBOXYLIC ACID PARENT COMPOUNDS (SHORT CHAIN)

ACRYLIC ACID
CAS NUMBER : 79-10-7
EINECS NUMBER : 201-177-9
OTHER CHEMICAL NAME(S):
Acroleic acid
2-Propenoic acid Acrylate Ethylenecarboxylic acid propene acid Propenoic acid Vinylformic Acid Acide acrylique (French) Acido acrilio (Spanish) Kyselina akrylova(Czech)
MELTING POINT(S): 12 C

CH2=CHCOOH (72.06)
ACRYLIC ACID

PROPIOLIC ACID
AS NUMBER : 471-25-0
EINECS NUMBER : 207-437-8
OTHER CHEMICAL NAME(S):
2-Propynoic acid Acetylenecarboxylic Acid Prop-2-ynoic acid Propargylic acid Propynoic acid
MELTING POINT(S): 16 C

CH°’CHCOOH (70.05)
PROPIOLIC ACID

METHACRYLIC ACID
CAS NUMBER : 79-41-4
EINECS NUMBER : 201-204-4
OTHER CHEMICAL NAME(S):
MAA 2-Methylenepropionic Acid 2-Methacrylic acid 2-Methyl-2-propenoic Acid Acide methacrylique (French) Acido metacrilico (Spanish) alpha-Methylacrylic acid Kyselina methakrylova (Czech)
MELTING POINT(S): 14 - 15 C

H2C=C(CH3)COOH (86.09)
METHACRYLIC ACID

CROTONIC ACID
CAS NUMBER : 3724-65-0
EINECS NUMBER : 223-077-4
OTHER CHEMICAL NAME(S):
beta-Methylacrylic acid 3-Methyl- Acrylic acid 2-Butenoic acid alpha-Butenoic acid 3-Methylacrylic acid alpha-Crotonic acid Kyselina krotonova
MELTING POINT(S): 73 C

CH3CH=CHCOOH (86.09)
CROTONIC ACID

ISOCROTONIC ACID
CAS NUMBER : 503-64-0
EINECS NUMBER :
OTHER CHEMICAL NAME(S):
(Z)-2-Butenoic acid (Z)-Crotonic acid cis-Crotonic Acid cis-2-Butenoic Acid
MELTING POINT(S):

CH3CH=CHCOOH (86.09)
ISOCROTONIC ACID

VINYLACETIC ACID
CAS NUMBER : 625-38-7
EINECS NUMBER : 210-892-5
OTHER CHEMICAL NAME(S):
3-Butenoic acid beta-Butenoic acid Ethenyl Acetic acid
MELTING POINT(S): -39 C

CH2=CHCH2COOH (86.09)
VINYLACETIC ACID

2-PENTENOIC ACID
CAS NUMBER : 626-98-2
EINECS NUMBER :
OTHER CHEMICAL NAME(S):
Pent-2-enoic acid
MELTING POINT(S):

C2H5CH=CHCOOH (100.12)
2-PENTENOIC ACID 

trans-2-PENTENOIC ACID
CAS NUMBER : 13991-37-2
EINECS NUMBER : 237-791-9
OTHER CHEMICAL NAME(S):
(E)-
2-Pentenoic acid (2E)-2-Pentenoic acid trans-Pent-2-enoic acid
MELTING POINT(S): 9 C

C2H5CH=CHCOOH (100.12)
trans-2-PENTENOIC ACID

3-PENTENOIC ACID
CAS NUMBER : 5204-64-8
EINECS NUMBER :
OTHER CHEMICAL NAME(S):
Pent-3-enoic acid
MELTING POINT(S):

CH3CH=CHCH2COOH (100.12)
3-PENTENOIC ACID

trans-3-PENTENOIC ACID
CAS NUMBER : 1617-32-9
EINECS NUMBER :
OTHER CHEMICAL NAME(S):
(E)-3
-Pentenoic acid trans-Pent-3-enoic acid
MELTING POINT(S):

CH3CH=CHCH2COOH (100.12)
trans-3-PENTENOIC ACID

ALLYLACETIC ACID
CAS NUMBER : 591-80-0

EINECS NUMBER : 209-732-7
OTHER CHEMICAL NAME(S):
4-Pentenoic acid Pent-4-enoic acid 4-PA
MELTING POINT(S): -22  C

CH2=CH2CH2CH2COOH (100.12)
ALLYLACETIC ACID

MALEIC ACID
CAS NUMBER : 110-16-7
EINECS NUMBER : 203-742-5
OTHER CHEMICAL NAME(S):
Hydroxysuccinic Acid
2-butenedioic acid cis-1,2-ethenedicarboxylic acid cis-2-butenedioic acid cis-butenedioic acid cis-ethene-1,2-dicarboxylic acid cis-maleic acid Malenic Acid Toxilic acid (Z)-1,2-ethenedicarboxylic acid (Z)-2-butenedioic acid
MELTING POINT(S): 138 C

HOOCCH=CHCOOH (116.07)
MALEIC ACID

FUMARIC ACID
CAS NUMBER : 110-17-8
EINECS NUMBER : 203-743-0
OTHER CHEMICAL NAME(S):
2-Butenedioic acid
1,2-Ethylenedicarboxylic Acid Allomaleic Acid trans-Butanedioic Acid (E)-2-Butenedioic acid trans-1,2-Ethylenedicarboxylic acid Allomaleic acid Boletic acid MELTING POINT(S): 299 C

HOOCCH=CHCOOH (116.07)
FUMARIC ACID

TIGLIC ACID
CAS NUMBER : 80-59-1
EINECS NUMBER : 201-295-0
OTHER CHEMICAL NAME(S):
(E)-2-Methyl-
Crotonic acid trans-alpha,beta-Dimethylacrylic Acid trans-2-Methyl-2-Butenoic acid trans-2-Methylcrotonic Acid trans-2,3-Dimethylacrylic Acid Cevadic acid Tiglinic acid 2,3-Dimethylacrylic acid (E)-2,3-Dimethylacrylic acid (2E)-2-Methyl-2-butenoic acid
MELTING POINT(S): 61 C

CH3CH2CH=CHCOOH (100.12)
TIGLIC ACID

ANGELIC ACID
CAS NUMBER : 565-63-9
EINECS NUMBER :
OTHER CHEMICAL NAME(S):
(Z)-2-Methyl-
Crotonic acid cis-alpha,beta-Dimethylacrylic Acid cis-2-Methyl-2-Butenoic acid cis-2-Methylcrotonic Acid cis-2,3-Dimethylacrylic Acid (Z)-2,3-Dimethylacrylic acid (2Z)-2-Methyl-2-butenoic acid
MELTING POINT(S):

CH3CH2CH=CHCOOH (100.12)
ANGELIC ACID

CITRACONIC ACID
CAS NUMBER : 498-23-7
EINECS NUMBER : 207-858-7
OTHER CHEMICAL NAME(S):
Methylmaleic acid cis-Methylbutenedioic acid methyl-Maleic acid Kyselina citrakonova 2-Methyl-2-butenedioic acid (2Z)-2-Methyl-2-butenedioic acid
MELTING POINT(S): 94 C

HOOCCH=CCH3COOH (130.10)
CITRACONIC ACID

MESACONIC ACID
CAS NUMBER : 498-24-8
EINECS NUMBER : 207-859-2
OTHER CHEMICAL NAME(S):
trans-1-Propene-1,2-Dicarboxylic acid trans-2-Methyl-2-Butenedioic acid Methylfumaric acid 2-Methylfumaric acid (E)-2-Methyl-2-butenedioic acid (E)-methyl-Butenedioic acid Methylfumaric acid, Mesaconate Kyselina mesakonova (2E)-2-Methyl-2-butenedioic acid
MELTING POINT(S): 200 C

HOOCCH=CCH3COOH (130.10)
MESACONIC ACID

 

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